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Published: 10 December 2022
Last updated: 28 January 2023

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1

De Bruyn, A., and M. Anteunis. "1H NMR Study of 2-Deoxy-D-Arabino-Hexopyranose (2-Deoxy Glucopyranose), 2-Deoxy-D-Lyxo-Hexopyranose (2-Deoxy Galactopyranose) and 2′-Deoxy Lactose. Shift Increment Studies in 2-Deoxy Carbohydrates." Bulletin des Sociétés Chimiques Belges 84, no. 12 (September 1, 2010): 1201–9. http://dx.doi.org/10.1002/bscb.19750841208.

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2

Krečmerová, Marcela, Hubert Hřebabecký, Milena Masojídková, and Antonín Holý. "Preparation of Purine 2'-Deoxy-5'-O-phosphonomethylnucleosides and 2'-Deoxy-3'-O-phosphonomethylnucleosides." Collection of Czechoslovak Chemical Communications 58, no. 2 (1993): 421–34. http://dx.doi.org/10.1135/cccc19930421.

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Sodium salt of 2'-deoxy-N6-dimethylaminomethylene-3'-O-(tetrahydro-2H-pyran-2-yl)adenosine (VIII) reacted with dibenzyl p-toluenesulfonyloxymethanephosphonate (Ia) to give dibenzyl ester of 2'-deoxy-N6-dimethylaminomethylene-5'-O-phosphonomethyl-3'-O-(tetrahydro-2H-pyran-2-yl)adenosine (XI) which after deprotection afforded the final 2'-deoxy-5'-O-phosphonomethyladenosine (XII). 2'-Deoxy-5'-O-hydroxymethanephosphonyladenosine (XIV) and 5'-O-benzyloxymethanephosphonyl-2'-deoxyadenosine (XIII) were isolated as a side product. The preparation of 2'-deoxy-5'-O-phosphonomethylguanosine (XVI) and protection of the starting nucleoside were analogous to those of compound XII. In the 2'-deoxy-3'-O-phosphonomethylnucleosides series, 2'-deoxy-3'-O-phosphonomethylcytidine (XXI) and 2'-deoxy-3'-O-phosphonomethyladenosine (XXVII) were prepared, using N4-benzoyl-5'-O-tert-butyldiphenylsilyl-2'-deoxycytidine (XVIII) and 5'-O-tert-butyldiphenylsilyl-2'-deoxy-N6-dimethylaminomethyleneadenosine (XXIV), respectively, as starting compounds.
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3

Ledvina, Miroslav, Daniel Zyka, Jan Ježek, Tomáš Trnka, and David Šaman. "New Effective Synthesis of (N-Acetyl- and N-Stearoyl-2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine, Analogs of GMDP with Immunopotentiating Activity." Collection of Czechoslovak Chemical Communications 63, no. 4 (1998): 577–89. http://dx.doi.org/10.1135/cccc19980577.

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Ethyl 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (5), prepared by benzylation of ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (4), was transformed by reaction with bromine into 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (6). Thioglycoside 5 in the presence of methyl triflate and glycosylbromide 6 in the presence of silver triflate were used as glycosyl donors for condensation with benzyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranoside (7), to give benzyl 2-acetamido-3-O-allyl-6-O-benzyl-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-deoxy-α-D-glucopyranoside (8). Its reductive dephthaloylation with NaBH4/AcOH afforded benzyl 2-acetamido-3-O-allyl-4-O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)- 6-O-benzyl-2-deoxy-α-D-glucopyranoside (11). Compound 11 was N-acylated to give benzyl 2-acetamido-4-O-(2-acylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-allyl-6-O-benzyl-2-deoxy-α-D-glucopyranosides (12a) or (12b). These compounds were converted into corresponding benzyl 2-acetamido-4-O-(2-acylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-6-O-benzyl-3-O-carboxymethyl-2-deoxy-α-D-glucopyranosides which, by condensation with H-L-Abu-D-isoGln(OBzl) followed by hydrogenolysis of protective benzyl groups, furnished glycopeptides 16a and 16b. Intramolecular O→N migration of the allyl protecting group followed by its reduction to the propyl residue by reaction of compound 8 with hydrazine or hydrazinium acetate, to give benzyl 2-acetamido-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-propylamino-β-D-glucopyranosyl)-6-O-benzyl-2-deoxy-α-D-glucopyranoside (9), is also described.
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4

Kefurt, Karel, Zdeňka Kefurtová, Věra Marková, and Karla Slívová. "Synthesis of 5-Amino-5-deoxypentonolactams." Collection of Czechoslovak Chemical Communications 61, no. 7 (1996): 1027–36. http://dx.doi.org/10.1135/cccc19961027.

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5-Azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose (4) and 5-azido-5-deoxy-1,2-O-isopropylidene-β-D-arabinofuranose (10) were prepared starting from D-xylose and D-arabinose, respectively. Using the oxidation-reduction way for the C-3 epimerization, 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (15) and 5-azido-5-deoxy-1,2-O-isopropylidene-β-D-lyxofuranose (17) were obtained from 4 and 10, respectively. The derivatives 4, 10, 15 and 17 afforded by acid hydrolysis, oxidation with bromine and catalytic hydrogenation successively the corresponding 5-azido-5-deoxy-D-pentofuranoses 6, 11, 18, 19, 5-azido-5-deoxy-D-pentonolactones 7, 12, 20, 21 and 5-amino-5-deoxy-D-pentonolactams 8, 13, 22, 23.
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5

Kennedy, Isaac A., Thomas Hemscheidt, James F. Britten, and Ian D. Spenser. "1-Deoxy-D-xylulose." Canadian Journal of Chemistry 73, no. 8 (August 1, 1995): 1329–37. http://dx.doi.org/10.1139/v95-164.

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1-Deoxy-D-xylulose (= 1-deoxy-D-theropentulose) is a precursor of thiamin (Vitamin B1) and of pyridoxine (Vitamin B6) in bacteria. The synthesis of a [2,3-13C2] bond-labeled sample of the compound, to be used for investigations of the biosynthesis of the two vitamins, is described. In aqueous solution 1-deoxy-D-xylulose exists mainly as the open chain ketone. In methanol solution the compound exists as a mixture of the open chain ketone and the two corresponding epimeric furanoses. In acid solution the compound yields a dimeric anhydride, di-β-1-deoxy-D-xylulofuranose 2,3′:3,2′-dianhydride, whose structure was established by X-ray crystallography. Keywords: [2,3-13C2]-1-deoxy-D-xylulose, di-β-1-deoxy-D-xylulofuranose 2,3′:3,2′-dianhydride, 5-O-benzyl-3,4-O-isopropylidene-1-deoxy-D-xylulose, 4-O-benzyl-2,3-O-isoproylidene-D-threose.
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6

Kato, N., F. Li, A. Mori, H. Takeshita, and T. Sassa. "9-Deoxy-15-hydroxy- and 9-Deoxy-19-hydroxycotylenol." Acta Crystallographica Section C Crystal Structure Communications 54, no. 8 (August 15, 1998): 1165–68. http://dx.doi.org/10.1107/s010827019800256x.

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7

Ibragimova, A. Sh, N. A. Ves’kina, I. V. Galyautdinov, and V. N. Odinokov. "Δ8(14)-14α-deoxy- and 14α-deoxy-14α-hydroperoxyecdysteroids." Russian Journal of Organic Chemistry 46, no. 11 (November 2010): 1735–40. http://dx.doi.org/10.1134/s1070428010110205.

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8

Ueno, Katsuhito, Shinichi Takamoto, Takeshi Miyairi, Tetsuro Morota, Ko Shibata, Arata Murakami, and Yutaka Kotsuka. "Multichannel Monitoring of Cerebral Circulatory and Oxygenation Status Using Optical Topography during Deep Hypothermic Retrograde Cerebral Perfusion." Vascular 12, no. 5 (September 2004): 325–30. http://dx.doi.org/10.1258/rsmvasc.12.5.325.

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In this study, we evaluated changes in the cerebral circulatory and oxygenation status during deep hypothermic total circulatory arrest (TCA) and retrograde cerebral perfusion (RCP) using optical topography, a form of multichannel near-infrared spectrophotometry, to monitor the broad area perfused by the middle cerebral artery. Seven patients underwent thoracic aortic surgery with TCA and RCP via the superior vena cava. Pressure-regulated RCP was performed under pH-stat. No postoperative neurologic complications occurred. Using optical topography, the relative changes in oxy-, deoxy-, and total hemoglobin (oxy-Hb, deoxy-Hb, total Hb) were simultaneously measured from 24 points in both hemispheres. Deoxy-Hb was used for evaluating the regional oxygenation status under RCP. The values of deoxy-Hb at the beginning of RCP were regarded as the basal values, and the rate of increase in deoxy-Hb per minute was calculated at each site. Deoxy-Hb/min during TCA was also calculated. In every case, both oxy-Hb and total Hb decreased and deoxy-Hb increased during TCA. When RCP was initiated, the decrease in oxy-Hb and the increase in deoxy-Hb were attenuated. The deoxy-Hb/min was significantly lower under RCP than during TCA in all portions. There was no significant difference of deoxy-Hb/min between any portions during RCP. Our results showed that the status of circulation and oxygenation might be uniform in the brain during RCP and better than that under TCA.
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9

Best, Wayne M., Robert V. Stick, and D. Matthew G. Tilbrook. "The Synthesis of Some Epoxyalkyl Deoxyhalo-β-cellobiosides." Australian Journal of Chemistry 50, no. 1 (1997): 13. http://dx.doi.org/10.1071/c96078.

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2,3-Epoxypropyl and 3,4-epoxybutyl 6′-deoxy-6′-iodo-β-cellobioside, together with 3,4-epoxybutyl 6′- deoxy-6′-fluoro-β-cellobioside, were prepared as putative inhibitors and reporter groups for events occurring at the active site of some β-glucan hydrolases. As well, related syntheses gave the previously unknown 6-deoxy-6-fluoro- and 6′-deoxy-6′-fluoro-cellobioses.
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10

Ledvina, Miroslav, Jiří Farkaš, Jaroslav Zajíček, Jan Ježek, and Milan Zaoral. "An alternative synthesis of O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-α-aminobutanoyl-D-isoglutamine." Collection of Czechoslovak Chemical Communications 54, no. 10 (1989): 2784–94. http://dx.doi.org/10.1135/cccc19892784.

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Silver triflate-promoted condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (VIII) with benzyl 2-acetamido-6-O-benzoyl-2-deoxy-3-O-(methoxycarbonyl)-methyl-α-D-glucopyranoside (IV) afforded benzyl 2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-6-O-benzoyl-2-deoxy-3-O-(methoxycarbonyl)methyl-α-D-glucopyranoside (IX) which, after deprotection, was converted into the acid XI. Condensation of acid XI with L-α-aminobutanoyl-D-isoglutamine benzyl ester and subsequent hydrogenolysis of the product XIII furnished compound XIV. Benzyl 2-acetamido-6-O-benzoyl-2-deoxy-3-O-(methoxycarbonyl)methyl-α-D-glucopyranoside (IV) was prepared by partial benzoylation of benzyl 2-acetamido-2-deoxy-3-O-(methoxycarbonyl)methyl-α-D-glucopyranoside (III) with benzoyl cyanide.
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11

Liu, Feng-Wu, Wenke Xu, Hui Yang, Yingju Liu, Yingchun Hua, Bin He, Xin Ning, Zhiyan Qin, and Hong-Min Liu. "Facile Approaches to 2-Deoxy-d-glucose and 2-Deoxy-α-d-glucopyranonucleosides from d-Glucal." Synthesis 49, no. 16 (June 7, 2017): 3686–91. http://dx.doi.org/10.1055/s-0036-1589501.

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Convenient and stereoselective methods for the preparation of 2-deoxy-d-glucose and purine 2-deoxy-α-d-glucopyranonucleosides were developed. Halogen-mediated O-glycosidation of d-glucal by bromine in MeOH followed by reductive removal of the halo group and hydrolysis of methoxy group by zinc in saturated aqueous sodium dihydrogen phosphate gave 2-deoxy-d-glucose. Treatment of 3,4,6-tri-O-acetyl-d-glucal with IBr and 2,6-dichloropurine based on haloetherification and subsequent reductive removal of iodine and deprotection allowed the isolation of purin-9-yl 2-deoxy-α-d-glucopyranonucleoside. Preparation of several purin-9-yl 2-deoxy-α-d-glucopyranoside derivatives is also reported. Their configuration was confirmed by single crystal X-ray analysis of the key intermediate 2,6-dichloro-9-(2-iodo-2-deoxy-α-d-glucopyranosyl)purine.
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12

Ziemniak, Marcin, Sylwia Pawlędzio, Anna Zawadzka-Kaźmierczuk, Paulina M. Dominiak, Damian Trzybiński, Wiktor Koźmiński, Rafał Zieliński, et al. "X-ray wavefunction refinement and comprehensive structural studies on bromo-substituted analogues of 2-deoxy-d-glucose in solid state and solution." RSC Advances 12, no. 14 (2022): 8345–60. http://dx.doi.org/10.1039/d1ra08312k.

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13

Veselý, Jan, Miroslav Ledvina, Jindřich Jindřich, Tomáš Trnka, and David Šaman. "Synthesis of 2-Amino-2-deoxy-β-D-galactopyranosyl-(1→4)-2-amino-2-deoxy-β-D-galactopyranosides: Using Various 2-Deoxy-2-phthalimido-D-galactopyranosyl Donors and Acceptors." Collection of Czechoslovak Chemical Communications 69, no. 10 (2004): 1914–38. http://dx.doi.org/10.1135/cccc20041914.

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A systematic study is presented of the efficiency of the most common glycosylation methods using standard 2-deoxy-2-phthalimidogalactopyranosyl donors ethyl 4-O-acetyl-3,6-di-O- benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (3a), 4-O-Acetyl-3,6-di-O-benzyl- 2-deoxy-2-phthalimido-β-D-galactopyranosyl bromide (4), 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl fluoride (5b), O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl) trichloroacetimidate (7) and ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside (8), pent-4-enyl 3,6-di-O-benzyl- and 3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside (10a) and (10b) and pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(trimethylsilyl)-β-D-galactopyranoside (11) as glycosyl acceptors in the synthesis of 2-amino-2-deoxy-β-D-galactopyranosyl-(1→4)-2-amino-2-deoxy-β-D-galactopyranosides 12, 16a and 17a. It was found that due to a low reactivity of the axial OH(4) group of glycosyl acceptors, disaccharides 16b and 17b with α(1→4) bond were also formed. The unexpected intermolecular migration of ethylsufanyl group from the reducing end of glycosyl acceptor 8 the reducing end of the activated form of glycosyl donor 4 in the glycosylation step to give ethylsulfanyl derivative 3a was proved. For preparation of the glycosyl donors and glycosyl acceptors with galacto configuration an approach based on epimerization of 4-O-mesyl derivatives of appropriate synthons with gluco configuration 2a and 2b was employed.
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14

El-Ghaouth, Ahmed, Joseph L. Smilanick, Michael Wisniewski, and Charles L. Wilson. "Improved Control of Apple and Citrus Fruit Decay with a Combination of Candida saitoana and 2-Deoxy-D-Glucose." Plant Disease 84, no. 3 (March 2000): 249–53. http://dx.doi.org/10.1094/pdis.2000.84.3.249.

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A combination of Candida saitoana with 0.2% 2-deoxy-D-glucose to control decay of apple, lemon, and orange fruit was evaluated. Growth of C. saitoana in vitro was reduced by 2-deoxy-D-glucose; however, in apple wounds, the yeast grew as well in the presence of 2-deoxy-D-glucose as in its absence. When applied to fruit wounds before inoculation, the combination of C. saitoana with 0.2% 2-deoxy-D-glucose was more effective in controlling decay of apple, orange, and lemon caused by Botrytis cinerea, Penicillium expansum, and P. digitatum than either C. saitoana or the application of a 0.2% solution of 2-deoxy-D-glucose alone. Increasing the concentration of 2-deoxy-D-glucose from 0.2 to 0.5% did not improve control significantly. The combination of C. saitoana with 0.2% 2-deoxy-D-glucose was also effective against infections established up to 24 h before treatment. When applied within 24 h after inoculation, the combination of C. saitoana with 0.2% 2-deoxy-D-glucose was very effective in controlling blue mold of apple and green mold of orange and lemon. The level of control of green mold was equivalent to imazalil treatment. When either C. saitoana or 0.2% 2-deoxy-D-glucose was applied within 24 h after inoculation, neither had an effect on disease development on apple, orange, or lemon, and the incidence of decay was similar to the water-treated control.
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15

Higashimoto, Yuji, Noritsugu Honda, Toshiyuki Yamagata, Akiko Sano, Osamu Nishiyama, Hiroyuki Sano, Takashi Iwanaga, et al. "Exertional dyspnoea and cortical oxygenation in patients with COPD." European Respiratory Journal 46, no. 6 (October 22, 2015): 1615–24. http://dx.doi.org/10.1183/13993003.00541-2015.

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This study was designed to investigate the association of perceived dyspnoea intensity with cortical oxygenation and cortical activation during exercise in patients with chronic obstructive pulmonary disease (COPD) and exertional hypoxaemia.Low-intensity exercise was performed at a constant work rate by patients with COPD and exertional hypoxaemia (n=11) or no hypoxaemia (n=16), and in control participants (n=11). Cortical oxyhaemoglobin (oxy-Hb) and deoxyhaemoglobin (deoxy-Hb) concentrations were measured by multichannel near-infrared spectroscopy. Increased deoxy-Hb is assumed to reflect impaired oxygenation, whereas decreased deoxy-Hb signifies cortical activation.Exercise decreased cortical deoxy-Hb in control and nonhypoxaemic patients. Deoxy-Hb was increased in hypoxaemic patients and oxygen supplementation improved cortical oxygenation. Decreased deoxy-Hb in the pre-motor cortex (PMA) was significantly correlated with exertional dyspnoea in control participants and patients with COPD without hypoxaemia. In contrast, increased cortical deoxy-Hb concentration was correlated with dyspnoea in patients with COPD and hypoxaemia. With the administration of oxygen supplementation, exertional dyspnoea was correlated with decreased deoxy-Hb in the PMA of COPD patients with hypoxaemia.During exercise, cortical oxygenation was impaired in patients with COPD and hypoxaemia compared with control and nonhypoxaemic patients; this difference was ameliorated with oxygen supplementation. Exertional dyspnoea was related to activation of the pre-motor cortex in COPD patients.
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16

El-Ghaouth, Ahmed, Charles L. Wilson, and Michael Wisniewski. "Antifungal Activity of 2-Deoxy-D-Glucose on Botrytis cinerea, Penicillium expansum, and Rhizopus stolonifer: Ultrastructural and Cytochemical Aspects." Phytopathology® 87, no. 7 (July 1997): 772–79. http://dx.doi.org/10.1094/phyto.1997.87.7.772.

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The effect of 2-deoxy-D-glucose on major postharvest pathogens was investigated at the ultrastructural and cytochemical level. Hyphae of Botrytis cinerea, Penicillium expansum,, and Rhizopus stolonifer grown in the absence of 2-deoxy-D-glucose were normal and showed no apparent cytological alterations. In the presence of 2-deoxy-D-glucose, however, these fungi exhibited severe cellular injuries ranging from cell wall disruption to cytoplasm disintegration. Although 2-deoxy-D-glucose caused cytoplasmic degeneration in the three fungi tested, cell wall alterations were exhibited only by B. cinerea and R. stolonifer. In the latter, the retraction of degenerated cytoplasm was often accompanied by the deposition of amorphous material in paramural spaces. Cytochemical study of fungal cell wall components showed that 2-deoxy-D-glucose caused a marked increase of chitin- and β-1,3-glucan—labeling in R. stolonifer and B. cinerea, indicating an interference of 2-deoxy-D-glucose with fungal wall biosynthesis. The observed cellular alterations indicate that 2-deoxy-D-glucose may also have affected other metabolic processes.
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17

Medonos, Ivan, Věroslava Kocíková, Jan Staněk, Alena Zobáčová, and Jiří Jarý. "Methyl esthers of methyl 2-deoxy-α- and β-D-threo-pentopyranoside." Collection of Czechoslovak Chemical Communications 51, no. 8 (1986): 1671–77. http://dx.doi.org/10.1135/cccc19861671.

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Methyl 2-deoxy-α- and β-D-threo-pentopyaranosides (Ia, IIa) were prepared. Various conditions for partial methylation of the β-anomer IIa were tried out, leading to methyl 2-deoxy-3-O-methyl-β-D-threo-pentopyranoside (IIc), methyl 2-deoxy-4-O-methyl-β-D-threo-pentopyranoside (IId) and methyl 2-deoxy-3,4-di-O-methyl-β-D-threo-pentopyranoside (IIe). The structures of the products were determined by means of 1H NMR.
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18

Jenkinson, Sarah F., K. Victoria Booth, Pushpakiran Gullapalli, Kenji Morimoto, Ken Izumori, George W. J. Fleet, and David J. Watkin. "1-Deoxy-L-mannitol (6-deoxy-L-mannitol orL-rhamnitol)." Acta Crystallographica Section E Structure Reports Online 64, no. 9 (August 6, 2008): o1705—o1706. http://dx.doi.org/10.1107/s1600536808024586.

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19

Kazakova, Ekaterina D., Dmitry V. Yashunsky, Elena A. Khatuntseva, and Nikolay E. Nifantiev. "Azidophenylselenylation of glycals towards 2-azido-2-deoxy-selenoglycosides and their application in oligosaccharide synthesis." Pure and Applied Chemistry 92, no. 7 (July 28, 2020): 1047–56. http://dx.doi.org/10.1515/pac-2020-0105.

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Abstract2-Amino-2-deoxy-pyranosyl units are important structural components of cell-wall polymers in prokaryotes, fungi and mammals. With respect to the need for development of novel and efficient vaccines and tools for serodiagnosis of infectious diseases, of particular interest are the oligosaccharide cell-wall antigens of pathogenic bacteria and fungi, which comprise 2-amino-2-deoxy-D-glucopyranose and 2-amino-2-deoxy-D-galactopyranose units as α- or β-anomers. Synthesis of N-acylated α-GlcN and α-GalN containing oligosaccharides is a special challenge due to the presence of a participating group at C2 which favors the formation of β- rather than α-glycoside bond. Herein we overview the efficient two-step approach for preparation of 1,2-cis-glycosides of 2-amino-2-deoxy-D-glucopyranose and 2-amino-2-deoxy-D-galactopyranose, which was recently developed in our laboratory. In the first step, an efficient and straightforward azidophenylselenylation procedure of glycals gives phenyl 2-azido-2-deoxy-1-selenoglycosides as versatile glycosyl donors. In the second step, these donors can be efficiently transformed into α- or β-glycosides depending on the choice of the solvent. In acetonitrile, total β-stereocontrol was achieved, and the use of diethyl ether as a solvent favouring α-stereoselectivity of glycosylations with phenyl 2-azido-2-deoxy-1-selenoglycosides. Besides, it was shown, that low reactivity and nucleophilicity of glycosyl acceptors which are glycosylated with phenyl 2-azido-2-deoxy-1-selenogalactosides facilitated the formation of α-GalN derivatives. To date, homogenous azidophenylselenylation of glycals and glycosylation with phenyl 2-azido-2-deoxy-1-seleno-α-D-glycopyranosides can be regarded as most useful tool for introduction of 2-amino-2-deoxy-D-glycopyranoside residues into complex synthetic oligosaccharides.
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20

Percival, M. David, and Stephen G. Withers. "Applications of enzymes in the synthesis and hydrolytic study of 2-deoxy-α-D-glucopyranosyl phosphate." Canadian Journal of Chemistry 66, no. 8 (August 1, 1988): 1970–72. http://dx.doi.org/10.1139/v88-317.

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The labile sugar phosphate 2-deoxy-α-D-glucopyranosyl phosphate has been synthesized enzymically in a two-step process from 2-deoxy-D-glucose-6-phosphate via an intermediate uridine 5′-diphospho-2-deoxy-D-glucose. Rate constants for acid-catalysed (1 M HClO4) hydrolysis at several temperatures were determined by using an enzymic assay to measure remaining substrate. The values obtained were consistent with that anticipated on the basis of known hydrolysis rates for alkyl- and aryl-2-deoxy-D-glucopyranosides.
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21

Rajaratnam, Premraj, Praveer Gupta, Peter Katavic, Krystle Kuipers, Ngoc Huyh, Sarah Ryan, Tania Falzun, et al. "Orthogonally Protected Monosaccharide Building Blocks for Solid Phase Production of Diversity Oriented Libraries." Australian Journal of Chemistry 63, no. 4 (2010): 693. http://dx.doi.org/10.1071/ch09480.

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The large scale synthesis of three orthogonally protected monosaccharide scaffolds suitable for use in the solid phase preparation of large diversity libraries is presented. Scaffolds based on 2-amino-2-deoxy-d-glucopyranose, 2-amino-2-deoxy-d-allopyranose, and 2,4-diamino-2,4-dideoxy-d-galactopyranose were prepared in good yield and with minimal chromatographic purification from commercially available methyl 2-azido-2-deoxy-1-thio-β-d-glucopyranose and methyl 2-amino-2-deoxy-1-thio-β-d-glucopyranose.
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22

Dey, Supriya, and Narayanaswamy Jayaraman. "Branching out at C-2 of septanosides. Synthesis of 2-deoxy-2-C-alkyl/aryl septanosides from a bromo-oxepine." Beilstein Journal of Organic Chemistry 8 (April 10, 2012): 522–27. http://dx.doi.org/10.3762/bjoc.8.59.

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This paper deals with the synthesis of 2-deoxy-2-C-alkyl/aryl septanosides. A range of such septanoside derivatives was synthesized by using a common bromo-oxepine intermediate, involving C–C bond forming organometallic reactions. Unsaturated, seven-membered septanoside vinyl bromides or bromo-oxepines, obtained through a ring expansion methodology of the cyclopropane derivatives of oxyglycals, displayed a good reactivity towards several acceptor moieties in C–C bond forming Heck, Suzuki and Sonogashira coupling reactions, thus affording 2-deoxy-2-C-alkyl/aryl septanosides. Whereas Heck and Sonogashira coupling reactions afforded 2-deoxy-2-C-alkenyl and -alkynyl derivatives, respectively, the Suzuki reaction afforded 2-deoxy-2-C-aryl septanosides. Deprotection and reduction of the 2-deoxy-2-alkenyl derivative afforded the corresponding 2-deoxy-2-C-alkyl septanoside free of protecting groups. The present study illustrates the reactivity of bromo-oxepine in the synthesis of hitherto unknown septanosides, branching out at C-2, through C–C bond formation with alkyl and aryl substituents.
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23

Schwartz, David A., Ho-Huat Lee, Jeremy P. Carver, and Jiri J. Krepinsky. "Syntheses of model oligosaccharides of biological significance. 4. Synthesis of a fucosylated N,N′-diacetylchitobioside and related oligosaccharides." Canadian Journal of Chemistry 63, no. 5 (May 1, 1985): 1073–79. http://dx.doi.org/10.1139/v85-182.

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The synthesis of two trisaccharides and one disaccharide containing L-fucose and 2-acetamido-2-deoxy-D-glucose is reported. Methyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside was glycosylated with a 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide. Removal of the phthalimido protecting groups by hydrazinolysis followed by N-acetylation and debenzylation yielded methyl N,N′-diacetylchitobioside 3′,4′,6′-triacetate. The latter was selectively fucosylated at the 6-position with 2,3,4-tri-O-benzyl-α-L-fucopyranosyl bromide to yield, after debenzylation and de-O-acetylation, methyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(α-L-fucopyranosyl)-β-D-glucopyranoside. When methyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside was fucosylated, its 6-O-and 4,6-di-O-(α-L-fucopyranosyl) derivatives were obtained by use of 1 and 2 equivalents, respectively, of the protected fucosyl bromide.
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24

Best, WM, RW Dunlop, RV Stick, and ST White. "All About 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucosyl Trichloroacetimidate." Australian Journal of Chemistry 47, no. 3 (1994): 433. http://dx.doi.org/10.1071/ch9940433.

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Treatment of 1,3,4,6-tetra-O-acetyl-2-(o-carboxybenzoylamino )-2-deoxy-β-D-glucose with ethyl chloroformate , followed by workup and treatment with methanol, did not give 1,3,4,6-tetra O-acetyl-2-deoxy-2-phthalimido-β-D-glucose as reported in the literature, but rather the methyl ester 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(o- methoxycarbonylbenzoylamino )-β-D-glucose. The formation of this methyl ester is believed to proceed via 1,3,4,6-tetra-O-acetyl-2-deoxy-2- [(3′-oxo-1′,3′-dihydroisobenzofuran-1′-ylidene)amino]-β-D-glucose which was also formed from the amido carboxylic acid by treatment with dicyclohexylcarbodiimide . Optimal procedures are given for the preparation of the title compound 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucosyl trichloroacetimidate.
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25

Ambrosio, Gabriella, Tasha Yuliandra, Bernhard Wuest, Monica Mazzarino, Xavier de la Torre, Francesco Botrè, Patrick Diel, Eduard Isenmann, and Maria Kristina Parr. "Urinary Elimination of Ecdysterone and Its Metabolites Following a Single-Dose Administration in Humans." Metabolites 11, no. 6 (June 9, 2021): 366. http://dx.doi.org/10.3390/metabo11060366.

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Ecdysterone is a phytosteroid widely discussed for its various pharmacological, growth-promoting, and anabolic effects, mediated by the activation of estrogen receptor beta (ERbeta). Performance-enhancement in sports was demonstrated recently, and ecdysterone was consequently included in the Monitoring Program, to detect potential patterns of misuse in sport. Only few studies on the pharmacokinetics of ecdysterone in humans have been reported so far. In this study, post-administration urine samples in twelve volunteers (single dose of 50 mg of ecdysterone) were analyzed using dilute-and-inject liquid-chromatography–tandem mass spectrometry. Identification and quantitation of ecdysterone and of two metabolites, 14-deoxy-ecdysterone and 14-deoxy-poststerone, was achieved. Ecdysterone was the most abundant analyte present in post-administration urine samples, detected for more than 2 days, with a maximum concentration (Cmax) in the 2.8–8.5 h urine (Cmax = 4.4–30.0 µg/mL). The metabolites 14-deoxy-ecdysterone and 14-deoxy-poststerone were detected later, reaching the maximum concentrations at 8.5–39.5 h (Cmax = 0.1–6.0 µg/mL) and 23.3–41.3 h (Cmax = 0.1–1.5 µg/mL), respectively. Sex-specific differences were not observed. Cumulative urinary excretion yielded average values of 18%, 2.3%, and 1.5% for ecdysterone, 14-deoxy-ecdysterone, and 14-deoxy-poststerone, respectively. Ecdysterone and 14-deoxy-ecdysterone were excreted following first-order kinetics with half-lives calculated with three hours, while pharmacokinetics of 14-deoxy-poststerone needs further evaluation.
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26

Otero, Iran, Holger Feist, Lidcay Herrera, Manfred Michalik, José Quincoces, and Klaus Peseke. "Nucleoside Analogues from Branched-Chain Pyranosides." Australian Journal of Chemistry 58, no. 2 (2005): 104. http://dx.doi.org/10.1071/ch04168.

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Reaction of (pyranosid-3-yl)ethanal 2 with ethynylmagnesium bromide or lithium phenylacetylide in THF afforded (2R,S)-1-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-d-altropyranosid-3-yl)but-3-yn-2-ols 3a and 3b, respectively. Oxidation of 3a and 3b yielded the 1-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-d-altropyranosid-3-yl)but-3-yn-2-ones 4a and 4b, which upon treatment with hydrazine and hydrazine derivatives formed the 3-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-d-altropyranosid-3-ylmethyl)pyrazoles 5a–5d. Compounds 4a and 4b also underwent reaction with amidinium and guanidinium salts under basic conditions to furnish the 4-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-d-altropyranosid-3-ylmethyl)pyrimidines 8a–8f. Furthermore, treatment of 4a and 4b with 2-aminobenzimidazole yielded the 2-(methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-d-altropyranosid-3-ylmethyl)benzo[4,5]imidazo[1,2-a]pyrimidines 11a and 11b. Deprotection of 5a and 8b in two steps afforded 3(5)-(methyl 3-deoxy-α-d-altropyranosid-3-ylmethyl)-1H(2H)-pyrazole 7 and 4-(methyl 3-deoxy-α-d-altropyranosid-3-ylmethyl)-2-phenylpyrimidine 10, respectively. Compound 11a was treated with AcOH/H2O to furnish 2-(methyl 2-O-benzyl-3-deoxy-α-d-altropyranosid-3-ylmethyl)benzo-[4,5]imidazo[1,2-a]pyrimidine 13.
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27

Lemieux, Raymond U., Rémy Cromer, and Ulrike Spohr. "Molecular recognition. VIII. The binding of the β-D-galactopyranosyl residue of the Lewis b human blood group determinant by the lectin IV of Griffonia simplicifolia and by a monoclonal anti-Lewis b antibody. Evidence for intramolecular hydrogen bonding." Canadian Journal of Chemistry 66, no. 12 (December 1, 1988): 3083–98. http://dx.doi.org/10.1139/v88-477.

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The 3b-deoxy, 4b-deoxy, 6b-deoxy, 6b-deoxy-6b-fluoro, 6b-chloro-6b-deoxy, and the 5b-des-hydroxymethyl derivatives of the Lewis b (αLFucd(1 → 2)βDGalb(1 → 3)[αLFucc(1 → 4)]βDGlcNAca-OMe) human blood group determinant were synthesized in order to examine the involvement of the βDGal b unit in the binding of the Leb-OMe tetrasaccharide both by the lectin IV of Griffonia simplicifolia and a hybridoma monoclonal anti-Leb antibody. The replacement of the CH2OH-5b group by hydrogen resulted in very weak binding by both the proteins, but the 6b-deoxy derivative was bound nearly as strongly as the parent compound in the case of the lectin but nine times more strongly in the case of the antibody. The 6b-fluoride was slightly more strongly bound than the 6b-deoxy derivative by both the proteins. On the other hand, the 6b-chloride was bound three times more strongly by the lectin but three times more weakly by the antibody than the 6b-deoxy derivative. The thermodynamic parameters for the binding of the 6b-deoxy derivative by the lectin as compared to those for Leb-OMe confirmed that OH-6b interacts within the combining site of the complex. The results appear to require that for both proteins the CH2OH-5b group becomes involved in nonpolar interactions within the combining site. It seems probable that OH-6b is accepted intramolecularly hydrogen bonded to O-5b in the case of the lectin but to OH-4b in the case of the antibody. The involvement of OH-3b, OH-4b, and OH-4c as the key polar grouping for the binding of Leb-OMe by the lectin and of OH-3b and OH-2d in the case of the antibody was reported previously.
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28

Sun, Zhi Dong, Zi Wen Gong, Chen Hu, Hai Yang Huang, Xi Chen, and Qiang Xiao. "Synthesis of an Isomeric Nucleoside Enantiomers of 1,3-bis(1'-deoxy-β-ribofuranose-2'-yl)-thymine." Advanced Materials Research 1094 (March 2015): 49–52. http://dx.doi.org/10.4028/www.scientific.net/amr.1094.49.

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The enantiomer isomeric nucleosides of 1,3-bis (1'-deoxy-β-ribofuranose-2'-yl)-thymine were synthesized from 1-deoxy-5-O-triphenylmethyl-ribose in high yield and selectivity. The key step is the coupling of 1-deoxy-5-O-triphenylmethyl-2,3-O-cyclosulphate-ribose and thymine using cesium carbonate as the base.
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29

Adachi, K., J. Pang, P. Konitzer, and S. Surrey. "Polymerization of recombinant hemoglobin F gamma E6V and hemoglobin F gamma E6V, gamma Q87T alone, and in mixtures with hemoglobin S." Blood 87, no. 4 (February 15, 1996): 1617–24. http://dx.doi.org/10.1182/blood.v87.4.1617.bloodjournal8741617.

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To further understand determinants for Hemoglobin (Hb) S polymerization, as well as the inhibitory mechanism of Hb F on Hb S polymerization, Hb F variants containing Val-gamma 6 (Hb F gamma E6V) or Val-gamma 6, Thr-gamma 87 (Hb F gamma E6V, gamma Q87T) were expressed in yeast. The oxy form of Hb F gamma E6V was about 10-fold less stable to mechanical agitation than native oxy Hb F, which is similar to stability differences comparing oxy Hb S and oxy Hb A. Deoxy Hb F gamma E6V showed approximately 20-fold decreased solubility compared with native deoxy Hb F in high phosphate buffer and formed gels like deoxy Hb S in low phosphate buffer, indicating that the Val- gamma 6 substitution decreases solubility of Hb F like Val-beta 6 in deoxy Hb S. Oversaturated deoxy Hb F gamma E6V polymerized without a delay time in low and high phosphate buffers, in contrast to deoxy Hb S, which is accompanied by a distinct delay time before polymerization. Deoxy Hb F gamma E6V, gamma Q87T also polymerized without a delay time like deoxy Hb F gamma E6V. These results suggest that deoxy Hb F gamma E6V gamma Q87T polymers are different from those of deoxy Hb S, and that contact sites differ from those of deoxy Hb S, even though both have the same primary donor (A3) and acceptor sites in the EF helix. These results also suggest that other amino acids in addition to beta 6 Val and amino acids in the F helix are critical for nucleation- controlled polymerization of deoxy Hb S. 1:1 mixtures of deoxy Hb S and either Hb F variant polymerized with a delay time when the concentrations for the Hb S/Hb F gamma E6V and Hb S/Hb F gamma E6V, gamma Q87T mixtures were about 2- and 1.5-fold, respectively, higher than that for Hb S. Logarithmic plots of delay time versus concentration for Hb S/Hb F gamma E6V mixtures showed the same straight line as the line for Hb S/Hb S beta T87Q mixtures, but values for Hb S/Hb F gamma E6V, gamma Q87T mixtures were intermediate between those for Hb S and Hb S/Hb F gamma E6V mixtures. A 1:1 mixture of deoxy Hb A and Hb F gamma E6V, gamma Q87T also polymerized, but exhibited biphasic kinetics, when the concentration was increased to more than 3.5-fold higher than that required for Hb S polymer formation. These results suggest that Gin-gamma 87 is a critical amino acid for exclusion of FS hybrids (alpha 2 beta S gamma) from nuclei formation with Hb S. Our findings also show that Val-gamma 6 in hybrids that form in mixtures of the Hb F variants with either Hb S or Hb A interacts with the hydrophobic acceptor pocket on the EF helix of an adjacent tetramer containing Thr-beta 87.
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30

Schwarz, Thomas, David Heß, and Peter Klüfers. "Metal chelation by the common 2-amino-2-deoxy-, 2-N-acetylamino-2-deoxy-, and 2-deoxy-hexoses." Dalton Transactions 39, no. 23 (2010): 5544. http://dx.doi.org/10.1039/c002711a.

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31

Petrakova, Eva, Ulrike Spohr, and Raymond U. Lemieux. "Molecular recognition IX. The synthesis of the H-type 2 human blood group determinant and congeners modified at the 6-position of the N-acetylglucosamine unit." Canadian Journal of Chemistry 70, no. 1 (January 1, 1992): 233–40. http://dx.doi.org/10.1139/v92-034.

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The synthesis of the methyl glycosides of the H-type 2 human blood group determinant (α-L-Fuc-(1c → 2b)-β-D-Gal-(1b → 4a)-β-D-GlcNAc-OMe) and its 6a-deoxy, 6a-O-methyl, 6a-chloro-6a-deoxy, 6a-deoxy-6a-fluoro, 6a-amino-6a-deoxy, 6a-acetamido-6a-deoxy, and 6a-deoxy-6a-pivalamido congeners is reported. The compounds were prepared to test the hypothesis that the binding of the H-type 2 trisaccharide by the lectin I of Ulexeuropaeus requires OH-6a to become intramolecularly hydrogen bonded to the neighboring O-5a ring atom. The results obtained in the binding studies are reported in an accompanying publication (Spohr, Paszkiewicz-Hnatiw, Morishima, and Lemieux) where it is demonstrated that the formation of the intramolecular hydrogen bond is not required for effective binding. In view of the results reported in another accompanying paper (Nikrad, Beierbeck, and Lemieux), OH-6a most likely remains in contact with the aqueous phase near the periphery of the combining site. Keywords: N-acetylglucosamine derivatives, H-type 2 blood group determinant and congeners, oligosaccharide synthesis.
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32

Nakanishi, H., K. Oguri, K. Yoshida, N. Itano, K. Takenaga, T. Kazama, A. Yoshida, and M. Okayama. "Structural differences between heparan sulphates of proteoglycan involved in the formation of basement membranes in vivo by Lewis-lung-carcinoma-derived cloned cells with different metastatic potentials." Biochemical Journal 288, no. 1 (November 15, 1992): 215–24. http://dx.doi.org/10.1042/bj2880215.

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This study addresses the characterization of heparan sulphates of the basement-membrane proteoglycans in tumour formed after the subcutaneous implantation of Lewis-lung-carcinoma-derived different metastatic clones (P29, LM12-3 and LM60-D6 clones with low, medium and high metastatic potentials respectively). Heparan sulphate proteoglycans (125-158 micrograms of hexuronate/g dry weight of tissue) were isolated from chondroitin ABC lyase digests of a proteoglycan fraction obtained after DEAE-Sephacel chromatography of tissue extracts. The proteoglycans were separated into three molecular species by Sepharose CL-4B chromatography followed by CsCl-density-gradient centrifugation: large proteoglycans with an estimated M(r) of 820,000-130,000, which consisted of two components with low (< 1.34 g/ml; PGII-M) and high (> 1.37 g/ml; PGII-B) density, and a small proteoglycan with an M(r) of less than 80,000 (PGIII). Of these, only the PGII-M proteoglycan (34-37 micrograms of hexuronate/g dry weight) reacted with the antiserum against proteoglycan of Engelbreth-Holm-Swarm-tumour basement membrane, and represented, therefore, a basement-membrane proteoglycan. Digestion with heparan sulphate lyases I and II of the heparan sulphates (M(r) 36,000) from the PGII-M proteoglycan of the three tumours resulted in almost complete depolymerization to give six unsaturated disaccharides identified as 2-acetamido-2-deoxy-4-O-(4-deoxy-alpha-L-threo-hex-4-enopyranosyluron ic acid)-D-glucose, 2-acetamido-2-deoxy-4-O-(4-deoxy-alpha-L-threo-hex-4-enopyranosyluron ic acid)-6-O-sulpho-D-glucose, 2-deoxy-2-sulphamino-4-O-(4-deoxy-alpha-L-threo-hex-4-enopyrano syluronic acid)-D-glucose, 2-deoxy-2-sulphamino-4-O-(4-deoxy-alpha-L-threo-hex-4-enopyrano syluronic acid)-6-O-sulpho-D-glucose, 2-deoxy-2-sulphamino-4-O-(4-deoxy-2-O-sulpho-alpha-L-threo-hex-4- enopyranosyluronic acid)-D-glucose and 2-deoxy-2-sulphamino-4-O-(4-deoxy-2-O-sulpho-alpha-L-threo-hex-4- enopyranosyluronic acid)-6-O-sulpho-D-glucose. Comparison of the relative amounts of these disaccharides produced from the three tumour-derived heparan sulphates demonstrated that the degree of sulphation of the heparan sulphates correlated with the degree of morphological organization of the tumour basement membranes; the heparan sulphate from the more highly metastatic tumour with more highly organized basement membrane exhibited a higher degree of overall sulphation along the glycosaminoglycan chains, which was due to an increased content of the three repeating disaccharides having 6-O-sulphated glucosamine residues.
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33

Drašar, Pavel, and Jiří Beránek. "2',3'-O-Carbonyl derivatives of 6-azauridine in the synthesis of its 5-substituted and 5'-deoxy derivatives." Collection of Czechoslovak Chemical Communications 52, no. 8 (1987): 2070–82. http://dx.doi.org/10.1135/cccc19872070.

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Preparation of 2',3'-O-carbonyl derivatives of 5'-deoxy-6-azauridine and 6-azauridine using 1,1'-carbonyldiimidazole has been elaborated. 5'-Chloro and 5'-bromo derivatives were prepared by treatment of the 5'-O-mesyl derivative with quaternary ammonium halides, 5'-chloro derivatives also by direct halogenation with thionyl chloride in hexamethylphosphortriamide or with tetrachloromethane, triphenyl phosphine, and dimethylformamide. Derivatives of 5'-bromo-6-azauridine were reduced with tributyltin hydride to 5'-deoxy-6-azauridine compounds. 6-Azauridine 2',3'-carbonate (IVa) and its 5'-derivatives IVc and IVe on treatment with imidazole in dimethylformamide afforded 2,2'-anhydronucleosides IIIa-IIIc. The 2,2'-anhydro-5'-deoxy compound IIIc underwent alkaline hydrolysis to 5'-deoxy-1-β-D-arabino-pentofuranosyl-6-azauracil (VIa). Treatment of 2,2'-anhydro-5'-deoxy-5'-chloro derivative IIIb with hydrogen chloride led to 2',5'-dichloro derivative If.
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34

Kollatos, Nikolaos, Christos Mitsos, Stella Manta, Niki Tzioumaki, Christos Giannakas, Tania Alexouli, Aggeliki Panagiotopoulou, Dominique Schols, Graciela Andrei, and Dimitri Komiotis. "Design, Synthesis, and Biological Evaluation of Novel C5-Modified Pyrimidine Ribofuranonucleosides as Potential Antitumor or/and Antiviral Agents." Medicinal Chemistry 16, no. 3 (April 17, 2020): 368–84. http://dx.doi.org/10.2174/1573406415666190225112950.

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Background: Nucleoside analogues are well-known antitumor, antiviral, and chemotherapeutic agents. Alterations on both their sugar and the heterocyclic parts may lead to significant changes in the spectrum of their biological activity and the degree of selective toxicity, as well as in their physicochemical properties. Methods: C5-arylalkynyl-β-D-ribofuranonucleosides 3-6, 3΄-deoxy 12-15, 3΄-deoxy-3΄-C-methyl- β-D-ribofurananucleosides 18-21 and 2΄-deoxy-β-D-ribofuranonucleosides 23-26 of uracil, were synthesized using a one-step Sonogashira reaction under microwave irradiation and subsequent deprotection. Results: All newly synthesized nucleosides were tested for their antitumor or antiviral activity. Moderate cytostatic activity against cervix carcinoma (HeLa), murine leukemia (L1210) and human lymphocyte (CEM) tumor cell lines was displayed by the protected 3΄-deoxy derivatives 12b,12c,12d, and the 3΄-deoxy-3΄-methyl 18a,18b,18c. The antiviral evaluation revealed appreciable activity against Coxsackie virus B4, Respiratory syncytial virus, Yellow Fever Virus and Human Coronavirus (229E) for the 3΄-deoxy compounds 12b,14, and the 3΄-deoxy-3΄-methyl 18a,18c,18d, accompanied by low cytotoxicity. Conclusion: This report describes the total and facile synthesis of modified furanononucleosides of uracil, with alterations on both the sugar and the heterocyclic portions. Compounds 12b,14 and 18a,c,d showed noticeable antiviral activity against a series of RNA viruses and merit further biological and structural optimization investigations.
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35

Roche, Camille J., Tatiana C. Balazs, Qiuying Chen, Juan C. Moreira, Joel M. Friedman, and Rhoda Elison Hirsch. "Hemoglobin E (β26Glu→Lys) Exhibits Altered Nitrite Reactivity." Blood 114, no. 22 (November 20, 2009): 2564. http://dx.doi.org/10.1182/blood.v114.22.2564.2564.

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Abstract Abstract 2564 Poster Board II-541 Hemoglobin (Hb) EE individuals exhibit a mild, chronic anemia while HbE/β thalassemia individuals show a range of clinical manifestations, including high morbidity, and death, often resulting from cardiac dysfunction. Yet, HbE (β26 Glu→Lys), known to be more unstable than HbA in vitro, remains an enigma in terms of its contributions to red blood cell (RBC) pathophysiological mechanisms. Considering the above and that pediatric HbE/β thalassemia patients exhibit endothelial dysfunction with oxidative stress, we consider the possibility that HbE is not as effective as HbA with respect to generating bioactive forms of nitric oxide (NO) that can limit endothelial dysfunction. Since reactions of Hb with nitrite are central to their capacity to generate bioactive NO, we compare HbA and HbE with respect to the reaction of nitrite with both the deoxy and oxy derivatives. Additionally, as a means of comparing redox potentials, we use L-cysteine as a biologically relevant reductant to compare HbA and HbE with respect to reduction of the aquomet derivative to the deoxy derivative. The redox potential has been shown to be a major determinant of nitrite reactivity for Hb. Reactions of purified oxy HbE and deoxy HbE at neutral pH in the presence of excess nitrite (∼4:1 nitrite: tetramer) compared to oxy and deoxy HbA are monitored by visible absorption spectroscopy. Since deoxy Hb is a nitrite reductase [deoxy Hb + nitrite → met Hb + NO], the reaction rate was assessed by the loss of the characteristic deoxy Hb absorption spectrum. The initial rate of reaction was significantly slower for deoxy HbE than deoxy HbA. Oxy Hb reacts with nitrite to form met Hb [simplified as, oxy Hb + nitrite → met (Fe+3)Hb + nitrate] and is followed by formation of the characteristic met Hb absorption spectrum. Under these in vitro conditions, the oxy HbE reaction with nitrite is complete at ∼120 secs and faster than oxy HbA (∼180 secs), while deoxy HbE shows a reaction with nitrite that is slower to reach completion (deoxy HbE∼1400 secs) compared to deoxy HbA (∼1000 secs). Consistent with known Hb-nitrite reactivity, the reaction with nitrite for both oxy HbE and oxy HbA is faster than their respective deoxy Hb reaction with nitrite. Met HbE is more rapidly reduced by L-cysteine to form deoxy HbE compared to HbA. The nitrite reaction rates and the redox ordering are consistent with HbE populations having a greater propensity to remain in the T state compared to comparable samples of HbA. In brief, under these conditions, all results are consistent with HbE being shifted more towards the T-state in the R↔T equilibrium compared to HbA. Structural evidence in support of an allosteric alteration in HbE is seen in the high resolution deoxy and oxy HbE crystallographic structures compared to HbA structures grown under the same crystal forming conditions [Protein Data Bank entries 1YVT, 1YVQ, 3DUT; Hirsch et al. (2008) Blood 112(11):540a]. Our findings will be discussed from at least three perspectives: an altered nitrite reactivity for HbE and its physiological relevance; support for the findings of Kavanaugh et al. (2005, Biochemistry) and others that the α1β1 interface undergoes significant changes in the Hb allosteric transition; and the allosteric transition involves a Hb T-state continuum. Disclosures: No relevant conflicts of interest to declare.
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36

Marcotte, Stéphane, Baudoin Gérard, Xavier Pannecoucke, Christian Feasson, and Jean-Charles Quirion. "Synthesis of 3′-Deoxy-3′-difluoromethyluridine and 2′-Deoxy-2′-difluoromethyluridine." Synthesis 2001, no. 06 (2001): 0929–33. http://dx.doi.org/10.1055/s-2001-13419.

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37

Guaragna, Annalisa, Daniele D’Alonzo, Concetta Paolella, and Giovanni Palumbo. "Synthesis of 1-deoxy-l-gulonojirimycin and 1-deoxy-l-talonojirimycin." Tetrahedron Letters 50, no. 18 (May 2009): 2045–47. http://dx.doi.org/10.1016/j.tetlet.2009.02.111.

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38

Aamlid, Kai H., Leslie Hough, and Anthony C. Richardson. "Synthesis of 1-deoxy-6-epicastanospermine and 1-deoxy-6,8a-diepicastanospermine." Carbohydrate Research 202 (July 1990): 117–29. http://dx.doi.org/10.1016/0008-6215(90)84075-6.

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39

Zhang, Wenhui, Bruce C. Noll, and Anthony S. Serianni. "3-Deoxy-β-D-ribo-hexopyranose (3-deoxy-β-D-glucopyranose)." Acta Crystallographica Section C Crystal Structure Communications 63, no. 10 (September 1, 2007): o578—o581. http://dx.doi.org/10.1107/s0108270107038553.

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40

Ledvina, Miroslav, David Šaman, and Jan Ježek. "Synthesis of O-(2-Deoxy-2-stearoylamino-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-α-aminobutanoyl-D-isoglutamine, a Lipophilic Disaccharide Analogue of MDP." Collection of Czechoslovak Chemical Communications 57, no. 3 (1992): 579–89. http://dx.doi.org/10.1135/cccc19920579.

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Partial N-deacetylation of compound II with barium hydroxide afforded benzyl 2-acetamido-3-O-allyl-4-O-(2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-6-O,-benzyl-2-deoxy-α-D-glucopyranoside (III) in high yield. Compound III was N-acylated with stearic acid in the presence of DCC and the obtained product was converted into benzyl 2-acetamido-6-O-benzyl-3-O-carboxymethyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-2-deoxy-2-stearoylamino-β-D-glucopyranosyl)-α-D-glucopyranoside (VII). Coupling of compound VII with L-α-aminobutanoyl-D-isoglutamine benzyl ester followed by hydrogenolysis of the product VIII afforded compound IX.
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41

Bass, L., W. Bodsch, P. J. Robinson, and M. O. Young. "Metabolites of 2-deoxyglucose in rat brain at 12-24 h: bounds on kinetic constants." American Journal of Physiology-Endocrinology and Metabolism 253, no. 4 (October 1, 1987): E453—E460. http://dx.doi.org/10.1152/ajpendo.1987.253.4.e453.

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Activities of 2-deoxy-D-glucose and its metabolites in rat brain were examined at 12, 16, 20, and 24 h after intraperitoneal injection of 14C-labeled 2-deoxy-D-glucose. Plasma radioactivity was monitored for 2 h before each of these determinations. As proportion of total brain radioactivity, 2-deoxy-D-glucose decreased monotonically from the unexpectedly high value of 22% at 12 h to 11% at 24 h after injection, 2-deoxy-D-glucose 6-phosphate decreased monotonically from 69% at 12 h to 23% at 24 h, and unphosphorylated products (of high and low molecular weight) increased from 10% at 12 h to 64% at 24 h. The data were analyzed in terms of a four-compartment model. Secure lower and upper bounds on the rate constant, k4*, for the dephosphorylation of 2-deoxy-D-glucose 6-phosphate were established: k4* was at least 0.0158 +/- 0.0014 . min-1 and at most 0.0385 +/- 0.0037 . min-1. If k4* is constant in time, then appreciable dephosphorylation occurs within the 45-min experimental period commonly used in the standard 2-deoxy-D-glucose method for estimating local cerebral glucose utilization. The possibility that the effective k4* is lower at such early times is reviewed in the light of a reanalysis of previously published data. Implications of these results for the 2-deoxy-D-glucose method are discussed from the points of view of numerical analysis and capillary heterogeneity.
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42

Nagel, Yvonne, and Wolfgang Beck. "Metallkomplexe mit biologisch wichtigen Liganden, XLIII Metallkomplexe mit ungeschützten acyclischen Monosaccharid-Derivaten (Amin-, Oxim-, Schiffbase-, Thiazolidin-und 1,3-Dithian-Liganden)/Metal Complexes with Biologically Important Ligands, XLIII Metal Complexes with Unprotected Acyclic Derivatives of Monosaccharides (Amine, Oxime, Schiffbase, Thiazolidine and 1,3-Dithiane Ligands)." Zeitschrift für Naturforschung B 41, no. 11 (November 1, 1986): 1447–54. http://dx.doi.org/10.1515/znb-1986-1121.

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Abstract The synthesis and spectroscopic data of palladium (II), platinum (II), nickel(II), cobalt(II), copper(II) and gold(I) complexes with D-glucose oxime, 2-amino-2-deoxy-D-glucose oxime, 1,2-diamino-1,2-deoxy-D-glucitole, L-cysteine-D-glucose, D-glucose trimethylene mercaptale. Schiffbases from 1,2-diamino-1,2-deoxy-D -glucitole and acetylacetone or from D-glucosone and 1.3-diaminopropane are reported.
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43

Durham, Timothy B., and William R. Roush. "Stereoselective Synthesis of 2-Deoxy-β-Galactosides via 2-Deoxy-2-bromo- and 2-Deoxy-2-iodo-galactopyranosyl Donors." Organic Letters 5, no. 11 (May 2003): 1871–74. http://dx.doi.org/10.1021/ol034393t.

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44

Robinson, Jared, Indrajit Banerjee, and Alexandra Leclézio. "2-Deoxy D-Glucose in COVID-19: Current Research Trends." Journal of College of Medical Sciences-Nepal 18, no. 1 (March 31, 2022): 80–84. http://dx.doi.org/10.3126/jcmsn.v18i1.37651.

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2-Deoxy D- glucose is a novel drug. It is an analogue of glucose which has innate therapeutic uses due to both its antiviral properties as well as its anti-neoplastic action. The SARS-CoV-2 virus binds to the host cell via the (S2) spike glycoprotein. Once viral entry has been gained into the host cell the virus hijacks the host’s intracellular machinery via 2 factors; 3CLproand NSP15. It has been shown through the use of Toxicity estimation software as well as via Molinspiration that 2-Deoxy D- glucose and its aforementioned isomers can effectively bind with 3CLpro and NSP15 and intern thus immobilize the SARS-CoV-2 virus via the incapacitation of its viral receptors. On a molecular level the 2-Deoxy D- glucose derivatives produce a H bond with the glutamine AA residues of the SARS-CoV-2 (S2) spike, as well form a Hydrogen bond with the 2 Deoxy D-glucose and proline residues of the SARS-CoV-2 protease. It is thus evident via both molecular and in silico studies that 2 Deoxy D- glucose and its isomers have the ability to offer further protection and or have imperative diminution capabilities in the treatment of patients with the COVID-19 infection. 2-Deoxy D- glucose has shown promising results in clinical trials and has produced faster recovery in hospitalized patients and abridged additional oxygen dependence in COVID-19 patients in various states across India. The scope and potential for the use of 2-Deoxy D- glucose in the treatment of COVID-19 is evident. It is therefore of great importance that further in vivo studies are conducted with 2-Deoxy D-glucose in order to expedite the process of bringing this potentially lifesaving drug to market.
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45

Offer, J., J. C. Metcalfe, and G. A. Smith. "The uptake of 3H-labelled monodeoxyfluoro-myo-inositols into thymocytes and their incorporation into phospholipid in permeabilized cells." Biochemical Journal 291, no. 2 (April 15, 1993): 553–60. http://dx.doi.org/10.1042/bj2910553.

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Monodeoxyfluoro-myo-inositols were applied to electropermeabilized and intact thymocyte preparations to study their metabolism and uptake in order to investigate their suitability as potential inhibitors of phosphoinositide-mediated cellular responses. Only three of the monodeoxyfluoro-myo-inositols were incorporated into the phospholipids of thymocytes: 1D-3-deoxy-3-fluoro-myo-inositol, 5-deoxy-5-fluoro-myo-inositol and 1D-6-deoxy-6-fluoro-myo-inositol, all of which were weaker substrates for phosphatidylinositol synthase than was myo-inositol. The 3-, 5- and 6-fluoro analogues also behaved as competitive inhibitors, with K1 values of 350 +/- 5 microM, 350 +/- 5 microM and 2.9 +/- 2 mM respectively, compared with a Km for myo-inositol of 31 +/- 4 microM. When incubated with electropermeabilized thymocyte preparations, these three analogues of myo-inositol all formed phospholipids with chromatographic properties which corresponded to those of substituted phosphatidylinositol and phosphatidylinositol monophosphate. The uptake of myo-inositol and of the monodeoxyfluoro-myo-inositols into intact thymocytes was studied by a dual-label technique. All the monodeoxyfluoro-myo-inositols were taken up to some extent, but only 2-deoxy-2-fluoro-myo-inositol and 1D-3-deoxy-3-fluoro-myo-inositol were actively concentrated. The monodeoxyfluoro-myo-inositols were also assayed for their ability to inhibit the uptake of myo-inositol into cells. Both 2-deoxy-2-fluoro-myo-inositol and 1D-3-deoxy-3-fluoro-myo-inositol were effective inhibitors of myo-inositol uptake. Furthermore, 1D-1-deoxy-1-fluoro-myo-inositol, which was not taken up actively, was an effective inhibitor of myo-inositol uptake. The three effective inhibitors all showed Ki values of approximately 150 microM, close to the apparent Km for inositol uptake of 180 microM, and the 4-, 5- and 6-fluoro analogues had Ki values in excess of 10 mM.
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46

Kefurt, Karel, Karel Čapek, Zdeňka Kefurtová, and Jiří Jarý. "Preparation of 6-amino-6-deoxy-D-altronic acid and their derivatives." Collection of Czechoslovak Chemical Communications 51, no. 2 (1986): 391–400. http://dx.doi.org/10.1135/cccc19860391.

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Methyl 6-azido-3,5-di-O-benzoyl-6-deoxy-α- and -β-D-glucofuranosides (IIIandIV), obtained by methanolysis of 1,2-O-isopropylidene derivative II were converted via 2-O-methanesulfonyl esters V and VI to methyl 2,3-anhydro-6-azido-6-deoxy-α- and -β-D-mannofuranosides (VII or VIII, respectively). Epoxide VII when submitted to alkaline hydrolysis gave methyl 6-azido-6-deoxy-α-D-altrofuranoside (IX) exclusively, while epoxide VIII afforded a mixture of methyl 6-azido-6-deoxy-β-D-furanosides of altro (X) and gluco(XI) configuration in a 5 : 4 ratio. Altrofuranosides IX and X were converted to 6-azido-6-deoxy-D-altrose (XII) the oxidation of which with bromine and catalytic reduction with hydrogen afforded amorphous amino acid XIV, characterized as its tetraacetyllactam XVI. The structural changes of the compounds from individual steps of the synthesis were checked by IR and 1H NMR spectra which are discussed.
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47

Hanessian, Stephen, Oscar M. Saavedra, Miguel A. Vilchis-Reyes, and Ana M. Llaguno-Rueda. "Synthesis of 4′-deoxy-4′-fluoro neamine and 4′-deoxy-4′-fluoro 4′-epi neamine." MedChemComm 5, no. 8 (2014): 1166–71. http://dx.doi.org/10.1039/c4md00072b.

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48

Lee, Jin W., Fang Deng, Walter G. Yeomans, Alfred L. Allen, Richard A. Gross, and David L. Kaplan. "Direct Incorporation of Glucosamine andN-Acetylglucosamine into Exopolymers byGluconacetobacter xylinus (=Acetobacter xylinum) ATCC 10245: Production of Chitosan-Cellulose and Chitin-Cellulose Exopolymers." Applied and Environmental Microbiology 67, no. 9 (September 1, 2001): 3970–75. http://dx.doi.org/10.1128/aem.67.9.3970-3975.2001.

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ABSTRACT Gluconacetobacter xylinus (=Acetobacter xylinum) ATCC 10245 incorporated 2-amino-2-deoxy-d-glucose (glucosamine) and 2-acetamido-2-deoxy-d-glucose (N-acetylglucosamine), but not 3-O-methyl-d-glucose or 2-deoxy-d-glucose into exopolymers. Incorporation was confirmed by gas chromatography with and without mass spectrometry, Fourier transform infrared, and 1H nuclear magnetic resonance. The average molar percentage of glucosamine andN-acetylglucosamine in the exopolymers was about 18%.
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49

Bird, P., D. H. Dolphin, and S. G. Withers. "The synthesis of protected 5-azido-5-deoxy-D-glucononitriles as precursors of glycosidase inhibitors." Canadian Journal of Chemistry 68, no. 2 (February 1, 1990): 317–22. http://dx.doi.org/10.1139/v90-045.

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The successful syntheses of 5-azido-2,3,4,6-tetra-O-benzyl-5-deoxy-D-glucononitrile and 2,3,4,6-tetra-O-benzyl-5-deoxy-5-trifluoroacetamido-D-glucononitrile starting from D-glucose are described. Unsuccessful attempts were made to convert these two compounds into a protected 5-amino-5-deoxy-D-glucononitrile and to subsequently cyclize them to an amidine analogue of glucose as a possible glycosidase inhibitor. Keywords: synthesis, amino-sugars, glycosidase inhibitors.
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50

Lin, Zhen-Jian, Tian-Jiao Zhu, Guo-Jian Zhang, Hong-Juan Wei, and Qian-Qun Gu. "Deoxy-cytochalasins from a marine-derived fungus Spicaria elegans." Canadian Journal of Chemistry 87, no. 3 (March 2009): 486–89. http://dx.doi.org/10.1139/v09-006.

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Treatment of Spicaria elegans with cytochrome P-450 inhibitor resulted in two new deoxy-cytochalasins, 7-deoxy-cytochalasin Z7 (1) and 7-deoxy-cytochalasin Z9 (2), which were recognized as plausible precursors of cytochalasins Z7 and Z9, respectively. Their structures were elucidated by spectroscopic methods and the absolute configuration of 1 was determined by the conventional Mosher ester method. Their cytotoxicities against two cancer cell lines were evaluated.
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