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Journal articles on the topic 'Furanoside'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

Gerbst, Alexey G., Vadim B. Krylov, Dmitry A. Argunov, Maksim I. Petruk, Arsenii S. Solovev, Andrey S. Dmitrenok, and Nikolay E. Nifantiev. "Influence of per-O-sulfation upon the conformational behaviour of common furanosides." Beilstein Journal of Organic Chemistry 15 (March 15, 2019): 685–94. http://dx.doi.org/10.3762/bjoc.15.63.

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The studies on the recently discovered pyranoside-into-furanoside rearrangement have led us to conformational investigations of furanosides upon their total sulfation. Experimental NMR data showed that in some cases drastic changes of the ring conformation occurred while sometimes only the conformation of the exocyclic C4–C5 linkage changed. Herein we describe a combined quantum chemical and NMR conformational investigation of three common monosaccharide furanosides as their propyl glycosides: α-mannose, β-glucose and β-galactose. Full exploration of the furanoside ring by means of ab initio calculations was performed and coupling constants were calculated for each of the low-energy conformers. The results demonstrated preferred trans-orientation of H4–H5 protons in the non-sulfated molecules which changed to gauche-orientation upon sulfation. The effect is less pronounced in the galactosides. For all the studied structures changes in the conformational distribution were revealed by quantum mechanical calculations, that explained the observed changes in intraring coupling constants occurring upon introduction of sulfates.

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2

Sanapala, Someswara Rao, and Suvarn S. Kulkarni. "One-pot synthesis of bicyclic sugar oxazolidinone from d-glucosamine." RSC Advances 5, no. 29 (2015): 22426–30. http://dx.doi.org/10.1039/c5ra02270c.

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Herein we report a one-pot and efficient method for the synthesis of a 1,2-cis fused furanoside bicyclic oxazolidinone derivative of d-glucosamine via pyranose to furanose conversion and concomitant cyclization involving the N-Troc group.

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3

Asres, Daniel D., and Hélène Perreault. "Preparation, isolation, and characterization of permethylated galactosides and fucosides." Canadian Journal of Chemistry 77, no. 3 (March 1, 1999): 319–25. http://dx.doi.org/10.1139/v99-019.

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Sugar analysis involving permethylation followed by methanolysis can lead to significant results, given that permethylated monosaccharide standards are available for comparison of spectral and chromatographic data. Such standards are not readily commercially available, especially the furanoside forms. This note describes the isolation and characterization of permethylated pyranoside and furanoside species of D(+)-galactose and L(-)-fucose. Separation of the isomers was optimized using a combination of column chromatography and continuous elution thin-layer chromatography (TLC). TLC, gas chromatography - mass spectrometry, and 1H nuclear magnetic resonance (NMR) spectroscopy were used as the characterization methods. The isolation of furanosides is emphasized, since no specific NMR data have been reported on those to date, while several reports have already discussed the structural aspects of pyranosides.Key words: permethylation, monosaccharide, GC-MS, TLC, NMR.

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4

Asres, Daniel Derbie, and Hélène Perreault. "Monosaccharide permethylation products for gas chromatography - mass spectrometry: how reaction conditions can influence isomeric ratios." Canadian Journal of Chemistry 75, no. 10 (October 1, 1997): 1385–92. http://dx.doi.org/10.1139/v97-166.

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Methylation analysis has been widely used for determination of carbohydrate structures by mass spectrometry. Permethylation of monosaccharides yields mixtures of anomeric pyranosides and furanosides. This paper discusses the influence of some of the permethylation reaction parameters on the proportions of isomeric products obtained. The ratios of three five- and six-membered ring products obtained from two permethylated monosaccharides, D-galactose and L-fucose, have been determined as a function of reaction parameters. The method of Ciucanu and Kerek (1) (methyl iodide in dimethyl sulfoxide (DMSO) in the presence of sodium hydroxide (NaOH)) was used as a starting point. The "conventional" method consists of mixing all of the reagents with the substrate and allowing the reaction to proceed with stirring. Both D-galactose and L-fucose under these conditions produced two main permethylated isomers, a furanoside and a pyranoside, along with two other minor isomeric components. We have investigated the effect on the proportion of products obtained of mixing DMSO, substrate, and NaOH for various times prior to the addition of methyl iodide. Results for D-galactose showed that shorter times enhanced the formation of permethylated furanoside isomers, while reducing the proportion of pyranosides. In other sets of experiments, the time and temperature of reaction, following the addition of methyl iodide, were studied. The indication is that 15 min are sufficient to produce complete methylation, with longer reaction times yielding the same results. Again for D-galactose, low reaction temperatures (ca. 10 °C) favored formation of furanoside products. Higher temperatures yielded higher pyranoside/furanoside ratios. Higher quantities of NaOH also favored formation of the main galactopyranoside product. As for L-fucose, the ratio of the main furanoside vs. pyranoside products obtained by permethylation varied in a way similar to permethylated galactoside. Thus, higher temperatures and longer reaction times favored the main fucopyranoside product. Gentler conditions (i.e., shorter reaction times and lower temperatures) significantly favored the formation of the main fucofuranoside product. These results are interesting as they show the possibility of controlling the relative abundance of permethylated isomers of fucose and galactose. They also constitute a warning to chemists who use methylation procedures in their analyses, to the effect that permethylation products may vary considerably if the reaction conditions are not carefully controlled. Keywords: glucose, galactose, fucose, TLC, GC–MS, permethylation, monosaccharides.

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5

Gerbst, Alexey G., Vadim B. Krylov, and Nikolay E. Nifantiev. "Conformational changes in common monosaccharides caused by per-O-sulfation." Pure and Applied Chemistry 91, no. 7 (July 26, 2019): 1223–29. http://dx.doi.org/10.1515/pac-2018-1212.

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Abstract Polysulfated carbohydrates play an important role in many biological processes because of their ability to bind to various protein receptors such as different growth factors, blood coagulation factors, adhesion lectins etc. Precise information about spatial organization of sulfated derivatives is of high demand for molecular modelling of such interactions as well as for understanding of the mechanism of pyranoside-into-furanoside rearrangement. In this review we summarize the changes recently revealed for the conformations of common pyranosides and furanosides upon total O-sulfation which were studied by means of NMR spectroscopy as well as molecular modelling. It was found that pentoses, being more flexible, undergo complete conformational chair inversion. Meanwhile, for hexoses the situation strongly depends on the monosaccharide configuration. Conformational changes are most pronounced in gluco-compounds though quantum chemical calculations helped to establish that no complete chair inversion occurred. In furanosides distortions of two types were observed: either the ring conformation or the conformation of the side chain changed. The presented data may be used for the analysis of chemical, physical and biological properties of sulfated carbohydrates.

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6

Argunov, D. A., V. B. Krylov, and N. E. Nifantiev. "Convergent synthesis of isomeric heterosaccharides related to the fragments of galactomannan from Aspergillus fumigatus." Organic & Biomolecular Chemistry 13, no. 11 (2015): 3255–67. http://dx.doi.org/10.1039/c4ob02634a.

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7

Egron, David, Thierry Durand, Arlene Roland, Jean-Pierre Vidal, and Jean-Claude Rossi. "C-Furanoside Synthesis via Intramolecular Cyclization." Synlett 1999, no. 4 (April 1999): 435–37. http://dx.doi.org/10.1055/s-1999-3157.

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8

Vinnitskiy, Dmitry Z., Vadim B. Krylov, Nadezhda E. Ustyuzhanina, Andrey S. Dmitrenok, and Nikolay E. Nifantiev. "The synthesis of heterosaccharides related to the fucoidan from Chordaria flagelliformis bearing an α-l-fucofuranosyl unit." Organic & Biomolecular Chemistry 14, no. 2 (2016): 598–611. http://dx.doi.org/10.1039/c5ob02040a.

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9

Hale, Karl J., Leslie Hough, Soraya Manaviazar, and Andrew Calabrese. "Rules and Stereoelectronic Guidelines for the Anionic Nucleophilic Displacement of Furanoside and Furanose O-Sulfonates." Organic Letters 17, no. 7 (March 17, 2015): 1738–41. http://dx.doi.org/10.1021/acs.orglett.5b00511.

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10

Krylov, Vadim B., Lucia Paulovičová, Ema Paulovičová, Yury E. Tsvetkov, and Nikolay E. Nifantiev. "Recent advances in the synthesis of fungal antigenic oligosaccharides." Pure and Applied Chemistry 89, no. 7 (July 26, 2017): 885–98. http://dx.doi.org/10.1515/pac-2016-1011.

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AbstractThe driving force for the constant improvement and development of new synthetic methodologies in carbohydrate chemistry is a growing demand for biologically important oligosaccharide ligands and neoglycoconjugates thereof for numerous biochemical investigations such as cell-to-pathogen interactions, immune response, cell adhesion, etc. Here we report our syntheses of the spacer-armed antigenic oligosaccharides related to three groups of the polysaccharides of the fungal cell-wall including α- and β-mannan, α- and β-glucan and galactomannan chains, which include new rationally designed synthetic blocks, efficient solutions for the stereoselective construction of glycoside bonds, and novel strategy for preparation of furanoside-containing oligosaccharides based on recently discovered pyranoside-into-furanoside (PIF) rearrangement.

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11

Linden, A., C. K. Lee, and X. Li. "A fused furanoside-1,4-lactone at 173K." Acta Crystallographica Section C Crystal Structure Communications 55, no. 4 (April 15, 1999): 642–44. http://dx.doi.org/10.1107/s0108270198016692.

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12

Sharma, Gangavaram V. M., Gonuguntla Anjaiah, Marumudi Kanakaraju, Bommeda Sudhakar, Deepak Chatterjee, and Ajit C. Kunwar. "Synthesis of a new β-amino acid with a 3-deoxy-l-ara furnaoside side chain: the influence of the side chain on the conformation of α/β-peptides." Organic & Biomolecular Chemistry 14, no. 2 (2016): 503–15. http://dx.doi.org/10.1039/c5ob01753j.

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13

Lemaire, Sébastien, Amandine Xolin, Charlotte Gozlan, and Vittorio Farina. "Stereoselective C-glycosylation of furanosyl halides with arylzinc reagents." Pure and Applied Chemistry 86, no. 3 (March 20, 2014): 329–33. http://dx.doi.org/10.1515/pac-2013-1029.

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Abstract Were are reporting a highly diastereoselective, transition-metal-free approach of C-aryl glycosides in the pyranoside and furanoside series by the direct coupling of glycosyl halides with diarylzinc reagents in a toluene/di-n-butyl ether solvent mixture.

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14

Taha, Hashem A., Michele R. Richards, and Todd L. Lowary. "Conformational Analysis of Furanoside-Containing Mono- and Oligosaccharides." Chemical Reviews 113, no. 3 (October 16, 2012): 1851–76. http://dx.doi.org/10.1021/cr300249c.

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15

Velty, Rachel, Thierry Benvegnu, Muriel Gelin, Eric Privat, and Daniel Plusquellec. "A convenient synthesis of disaccharides containing furanoside units." Carbohydrate Research 299, no. 1-2 (March 1997): 7–14. http://dx.doi.org/10.1016/s0008-6215(96)00268-6.

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16

Krylov, Vadim B., Dmitry A. Argunov, and Nikolay E. Nifantiev. "Pyranoside-into-furanoside rearrangement of D-glucuronopyranoside derivatives." Mendeleev Communications 26, no. 6 (November 2016): 483–84. http://dx.doi.org/10.1016/j.mencom.2016.11.007.

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17

Gerbst, Alexey G., Vadim B. Krylov, Dmitry A. Argunov, Andrey S. Dmitrenok, and Nikolay E. Nifantiev. "Driving Force of the Pyranoside-into-Furanoside Rearrangement." ACS Omega 4, no. 1 (January 14, 2019): 1139–43. http://dx.doi.org/10.1021/acsomega.8b03274.

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18

McAuliffe, Joseph C., and Ole Hindsgaul. "Use of Acyclic Glycosyl Donors for Furanoside Synthesis." Journal of Organic Chemistry 62, no. 5 (March 1997): 1234–39. http://dx.doi.org/10.1021/jo9618583.

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19

Krishnudu, Kasireddy, Palakodety Radha Krishna, and Hari Babu Mereyala. "Pd(II)Cl2 mediated oxidative cycllsation of some 3-hydroxy 4-vinyl furanoside derivatives to synthetically valuable bis-furanosides." Tetrahedron Letters 37, no. 33 (August 1996): 6007–10. http://dx.doi.org/10.1016/0040-4039(96)01261-0.

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20

KRISHNUDU, K., P. R. KRISHNA, and H. B. MEREYALA. "ChemInform Abstract: PdCl2-Mediated Oxidative Cyclization of Some 3-Hydroxy-4-vinyl- furanoside Derivatives to Synthetically Valuable Bis-Furanosides." ChemInform 27, no. 48 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199648226.

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21

Benning, Rajdeep K., Helen M. I. Osborn, and Andrea Turkson. "Regioselective Beckmann rearrangements of furanoside and pyranoside-derived oximes." Tetrahedron: Asymmetry 22, no. 1 (January 2011): 109–16. http://dx.doi.org/10.1016/j.tetasy.2010.11.031.

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22

Lee, Eun, and Cheol Min Park. "C-furanoside synthesis via radical cyclisation of β-alkoxyacrylates." J. Chem. Soc., Chem. Commun., no. 3 (1994): 293–94. http://dx.doi.org/10.1039/c39940000293.

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23

Guimet, Eugeni, Montserrat Diéguez, Aurora Ruiz, and Carmen Claver. "Pd-catalyzed asymmetric allylic alkylation using furanoside diphosphinite ligands." Inorganica Chimica Acta 358, no. 13 (September 2005): 3824–28. http://dx.doi.org/10.1016/j.ica.2005.06.004.

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24

Ray, Ankur, and Sabiha Khan. "Convergent Synthesis of Novel Mono- and Di-substituted 1,2-Isopropylideneglucofuranose Appended Dendrimers with a Ferrocene Core and their Electrochemical Studies." Synlett 29, no. 10 (April 10, 2018): 1367–72. http://dx.doi.org/10.1055/s-0037-1609490.

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Ferrocene-cored dendrimers incorporating 1,2-isopropylidenefuranose capped furanoside branches were synthesized and their electrochemical properties were studied. It was observed that the dendritic environment in the ferrocene dendrimers increased the E 1/2 values with increase in bulk of the dendrimer, as expected. The reversible nature of the redox process was maintained in all the dendrimers.

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25

Maier, Martin E., and Tilmann Brandstetter. "Synthesis of an oxabicyclo[7.2.1] enediyne from a furanoside derivative." Tetrahedron Letters 33, no. 49 (1992): 7511–14. http://dx.doi.org/10.1016/s0040-4039(00)60810-9.

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26

Diéguez, Montserrat, Aurora Ruiz, and Carmen Claver. "Chiral furanoside phosphite–phosphoroamidites: new ligands for asymmetric catalytic hydroformylation." Tetrahedron: Asymmetry 12, no. 20 (November 2001): 2827–34. http://dx.doi.org/10.1016/s0957-4166(01)00489-x.

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27

Diéguez, Montserrat, Aurora Ruiz, and Carmen Claver. "Tunable furanoside diphosphite ligands. A powerful approach in asymmetric catalysis." Dalton Trans., no. 15 (2003): 2957–63. http://dx.doi.org/10.1039/b303303a.

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28

Taha, Hashem A., Michele R. Richards, and Todd L. Lowary. "ChemInform Abstract: Conformational Analysis of Furanoside-Containing Mono- and Oligosaccharides." ChemInform 44, no. 17 (April 4, 2013): no. http://dx.doi.org/10.1002/chin.201317278.

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29

MCAULIFFE, J. C., and O. HINDSGAUL. "ChemInform Abstract: Use of Acyclic Glycosyl Donors for Furanoside Synthesis." ChemInform 28, no. 28 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199728175.

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30

VELTY, R., T. BENVEGNU, M. GELIN, E. PRIVAT, and D. PLUSQUELLEC. "ChemInform Abstract: A Convenient Synthesis of Disaccharides Containing Furanoside Units." ChemInform 28, no. 27 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199727230.

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31

Shi, Zhizhong, Lili Sun, and Chunbao Li. "Solvent Polarity-Controlled Selective Synthesis of Methyl Pyranoside and Furanoside." Journal of Agricultural and Food Chemistry 62, no. 14 (March 26, 2014): 3287–92. http://dx.doi.org/10.1021/jf500144b.

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32

Pàmies, Oscar, Gino P. F. van Strijdonck, Montserrat Diéguez, Sirik Deerenberg, Gemma Net, Aurora Ruiz, Carmen Claver, Paul C. J. Kamer, and Piet W. N. M. van Leeuwen. "Modular Furanoside Phosphite Ligands for Asymmetric Pd-Catalyzed Allylic Substitution." Journal of Organic Chemistry 66, no. 26 (December 2001): 8867–71. http://dx.doi.org/10.1021/jo0159284.

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33

Hardacre, Christopher, Ivano Messina, Marie E. Migaud, Kerry A. Ness, and Sarah E. Norman. "1,2-Cyclic sulfite and sulfate furanoside diesters: improved syntheses and stability." Tetrahedron 65, no. 32 (August 2009): 6341–47. http://dx.doi.org/10.1016/j.tet.2009.06.013.

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34

Guimet, Eugeni, Montserrat Diéguez, Aurora Ruiz, and Carmen Claver. "Furanoside thioether–phosphinite ligands for Pd-catalyzed asymmetric allylic substitution reactions." Tetrahedron: Asymmetry 16, no. 5 (March 2005): 959–63. http://dx.doi.org/10.1016/j.tetasy.2004.11.094.

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35

Diéguez, Montserrat, Oscar Pàmies, and Carmen Claver. "Furanoside thioether–phosphinite ligands for Rh-catalyzed asymmetric hydrosilylation of ketones." Tetrahedron: Asymmetry 16, no. 23 (November 2005): 3877–80. http://dx.doi.org/10.1016/j.tetasy.2005.10.009.

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36

Nifantiev, Nikolay, Vadim Krylov, Dmitry Argunov, Dmitry Vinnitskiy, Alexey Gerbst, Nadezhda Ustyuzhanina, and Andrey Dmitrenok. "The Pyranoside-into-Furanoside Rearrangement of Alkyl Glycosides: Scope and Limitations." Synlett 27, no. 11 (April 6, 2016): 1659–64. http://dx.doi.org/10.1055/s-0035-1561595.

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37

LEE, E., and C. M. PARK. "ChemInform Abstract: C-Furanoside Synthesis via Radical Cyclisation of β- Alkoxyacrylates." ChemInform 25, no. 23 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199423227.

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38

Lak, Parnian, Spandana Makeneni, Robert J. Woods, and Todd L. Lowary. "Specificity of Furanoside-Protein Recognition through Antibody Engineering and Molecular Modeling." Chemistry - A European Journal 21, no. 3 (November 20, 2014): 1138–48. http://dx.doi.org/10.1002/chem.201405259.

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39

DENİZALTI, Serpil, Fatma ÇETİN TELLİ, Selin YILDIRAN, Azize Yeşim SALMAN, and Bekir ÇETİNKAYA. "Newly synthesized furanoside-based NHC ligands for the arylation of aldehydes." TURKISH JOURNAL OF CHEMISTRY 40 (2016): 689–97. http://dx.doi.org/10.3906/kim-1603-95.

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40

Casali, Emanuele, Sirwan T. Othman, Ahmed A. Dezaye, Debora Chiodi, Alessio Porta, and Giuseppe Zanoni. "Highly Stereoselective Glycosylation Reactions of Furanoside Derivatives via Rhenium (V) Catalysis." Journal of Organic Chemistry 86, no. 11 (May 25, 2021): 7672–86. http://dx.doi.org/10.1021/acs.joc.1c00706.

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41

Yan, Tu-Hsin, Hong-Jay Lo, and Yuan-Kang Chang. "A C2-Symmetric Pool Based Synthesis of the Furanoside of Hygromycin A." HETEROCYCLES 86, no. 1 (2012): 687. http://dx.doi.org/10.3987/com-12-s(n)19.

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42

Pàmies, Oscar, Gemma Net, Aurora Ruiz, and Carmen Claver. "Asymmetric hydroformylation of styrene catalyzed by furanoside phosphine–phosphite–Rh(I) complexes." Tetrahedron: Asymmetry 12, no. 24 (January 2002): 3441–45. http://dx.doi.org/10.1016/s0957-4166(02)00030-7.

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43

Ray, Ankur, and Subir Ghorai. "Ferrocene cored dendrimers incorporating anthracene capped furanoside branches: synthesis and photophysical studies." Tetrahedron Letters 52, no. 23 (June 2011): 2980–83. http://dx.doi.org/10.1016/j.tetlet.2011.03.137.

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44

MAIER, M. E., and T. BRANDSTETTER. "ChemInform Abstract: Synthesis of an Oxabicyclo(7.2.1) Enediyne from a Furanoside Derivative." ChemInform 24, no. 17 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199317083.

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45

Pamies, Oscar, Gino P. F. van Strijdonck, Montserrat Dieguez, Sirik Deerenberg, Gemma Net, Aurora Ruiz, Carmen Claver, Paul C. J. Kamer, and Piet W. N. M. van Leeuwen. "ChemInform Abstract: Modular Furanoside Phosphite Ligands for Asymmetric Pd-Catalyzed Allylic Substitution." ChemInform 33, no. 26 (May 21, 2010): no. http://dx.doi.org/10.1002/chin.200226110.

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46

Guimet, Eugeni, José Parada, Montserrat Diéguez, Aurora Ruiz, and Carmen Claver. "Asymmetric hydroformylation of vinyl arenes catalyzed by furanoside diphosphinites-Rh(I) complexes." Applied Catalysis A: General 282, no. 1-2 (March 2005): 215–20. http://dx.doi.org/10.1016/j.apcata.2004.12.013.

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47

Wilson, Lawrence J., Michael W. Hager, Yahya A. El-Kattan, and Dennis C. Liotta. "Nitrogen Glycosylation Reactions Involving Pyrimidine and Purine Nucleoside Bases with Furanoside Sugars." Synthesis 1995, no. 12 (December 1995): 1465–79. http://dx.doi.org/10.1055/s-1995-4142.

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48

Majdecki, Maciej, Janusz Jurczak, and Tomasz Bauer. "Palladium-Catalyzed Enantioselective Allylic Substitution in the Presence of Monodentate Furanoside Phosphoramidites." ChemCatChem 7, no. 5 (January 21, 2015): 799–807. http://dx.doi.org/10.1002/cctc.201402933.

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49

Diéguez, Montserrat, Oscar Pàmies, Aurora Ruiz, and Carmen Claver. "Synthesis and structural studies of rhodium(I)-catalytic precursors containing two furanoside diphosphines." Journal of Organometallic Chemistry 629, no. 1-2 (June 2001): 77–82. http://dx.doi.org/10.1016/s0022-328x(01)00819-1.

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50

Islam, Shahidul M., Brandon Havranek, Zahin Ibnat, and Pierre-Nicholas Roy. "New Insights into the Role of Hydrogen Bonding in Furanoside Binding to Protein." Journal of Physical Chemistry B 124, no. 10 (February 19, 2020): 1919–27. http://dx.doi.org/10.1021/acs.jpcb.9b11924.

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