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1

Skidmore, J. A., M. Billah et N. M. Loskutoff. « Developmental competence in vitro and in vivo of cryopreserved, hatched blastocysts from the dromedary camel (Camelus dromedarius) ». Reproduction, Fertility and Development 16, no 6 (2004) : 605. http://dx.doi.org/10.1071/rd03094.

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The present paper describes experiments designed to investigate methods for cryopreserving embryos from dromedary camels. Because preliminary studies had shown ethanediol to be the best cryoprotectant to use for camel embryos, the current experiments were performed to determine the minimum exposure time to 1.5 m ethanediol required to achieve cryoprotection. The uteri of 30 donor camels were flushed non-surgically 8 days after mating. Embryos were recovered and 158 were assigned to one of three groups, which were exposed to 1.5 m ethanediol for either 10 min (n = 67), 5 min (n = 51) or 1 min (n = 40). Embryos were subsequently thawed and rehydrated by expelling either directly into holding medium (HM; HEPES-buffered Tyrode's medium containing sodium lactate and 3 mg mL−1 bovine serum albumin, 10% fetal calf serum, 100 IU mL−1 penicillin G, 100 μg mL−1 streptomycin and 25 μg mL−1 amphotercin B) or initially into HM containing 0.2 m sucrose for 5 or 10 min. The survival rate of all embryos immediately post-thawing, as judged by the morphological appearance of the embryos, was high (91%), but was greatly reduced after 2 h culture (59%). Ninety-two embryos were transferred to recipient camels resulting in 18 viable fetuses (1 min ethanediol exposure, n = 1/15; 5 min ethanediol exposure, n = 3/34; 10 min ethanediol exposure, n = 14/43). Of the embryos rehydrated directly in HM, six of 65 resulted in viable fetuses and those rehydrated initially in 0.2 m sucrose for 5 or 10 min resulted in nine of 47 and three of 46 fetuses respectively. From these experiments, we conclude that camel embryos can be cryopreserved using ethanediol as a cryoprotectant when the embryos are cooled slowly (to 33°C) before being plunged into liquid nitrogen for storage.
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Heppke, G., D. Lötzsch et F. Oestreicher. « Chirale Dotierstoffe mit außergewöhnlich hohem Verdrillungsvermögen ». Zeitschrift für Naturforschung A 41, no 10 (1 octobre 1986) : 1214–18. http://dx.doi.org/10.1515/zna-1986-1006.

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Mesogenic chiral esters of 1-phenyl-1,2-ethandiol, 1-cyclohexyl-1,2-ethanediol, 1,2-diphenyl- 1,2-ethanediol, 1,1´-bi-2-naphthol, 1-phenylethanol, 1-phenyl-2,2,2-trifluorethanol and 1-(9- anthryl)-2,2,2-trifluorethanol were synthesized. The temperature dependence of the molecular twisting power was determined in the nematic wide range mixture RO-TN 404. All compounds show good solubility and unusual high values of the molecular twisting power.
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Leonelli, Francesca, Irene Piergentili, Giulio Lucarelli, Luisa Maria Migneco et Rinaldo Marini Bettolo. « Unexpected Racemization in the Course of the Acetalization of (+)-(S)-5-Methyl-Wieland–Miescher Ketone with 1,2-Ethanediol and TsOH under Classical Experimental Conditions ». International Journal of Molecular Sciences 20, no 24 (5 décembre 2019) : 6147. http://dx.doi.org/10.3390/ijms20246147.

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(+)-(S) and (−)-(R)-5-methyl-Wieland-Miescher ketone (+)-1 and (−)-1, are important synthons in the diastereo and enantioselective syntheses of biological and/or pharmacological interesting compounds. A key step in these syntheses is the chemoselective C(1)O acetalization to (+)-5 and (−)-5, respectively. Various procedures for this transformation have been described in the literature. Among them, the classical procedure based on the use of 1,2-ethanediol and TsOH in refluxing benzene in the presence of a Dean-Stark apparatus. Within our work on bioactive natural products, it occurred to us to observe the partial racemization of (+)-5 in the course of the acetalization of (+)-1 by means of the latter methodology. Aiming to investigate this drawback, which, to our best knowledge, has no precedents in the literature, we acetalized with 1,2-ethanediol and TsOH in refluxing benzene and in the presence of a Dean–Stark apparatus under various experimental conditions, enantiomerically pure (+)-1. It was found that the extent of racemization depends on the TsOH/(+)-1 and 1,2-ethanediol/(+)-1 ratios. Mechanism hypotheses for this partial and unexpected racemization are provided.
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Peng, Fei, Ying Zhao, Fang-Zhou Li, Xiao-Yang Ou, Ying-Jie Zeng, Min-Hua Zong et Wen-Yong Lou. « Highly enantioselective resolution of racemic 1-phenyl-1,2-ethanediol to (S)-1-phenyl-1,2-ethanediol by Kurthia gibsonii SC0312 in a biphasic system ». Journal of Biotechnology 308 (janvier 2020) : 21–26. http://dx.doi.org/10.1016/j.jbiotec.2019.11.012.

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Liu, Xiaolei, Min Wei, Feng Li et Xue Duan. « Intraparticle diffusion of 1-phenyl-1, 2-ethanediol in layered double hydroxides ». AIChE Journal 53, no 6 (2007) : 1591–600. http://dx.doi.org/10.1002/aic.11184.

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Yi, Wenwen, Le Qin, Xiao-Yuan Lian et Zhizhen Zhang. « New Antifungal Metabolites from the Mariana Trench Sediment-Associated Actinomycete Streptomyces sp. SY1965 ». Marine Drugs 18, no 8 (24 juillet 2020) : 385. http://dx.doi.org/10.3390/md18080385.

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New streptothiazolidine A (1), streptodiketopiperazines A (2) and B (3), and (S)-1-(3-ethylphenyl)-1,2-ethanediol (4), together with eight known compounds (5–12), were isolated from the Mariana Trench sediment-associated actinomycete Streptomyces sp. SY1965. The racemic mixtures of (±)-streptodiketopiperazine (2 and 3) and (±)-1-(3-ethylphenyl)-1,2-ethanediol (4 and 5) were separated on a chiral high-performance liquid chromatography (HPLC) column. Structures of the new compounds were elucidated by their high-resolution electrospray ionization mass spectroscopy (HRESIMS) data and extensive nuclear magnetic resonance (NMR) spectroscopic analyses. Streptothiazolidine A is a novel salicylamide analogue with a unique thiazolidine-contained side chain and its absolute configuration was established by a combination of nuclear Overhauser effect spectroscopy (NOESY) experiment, electronic circular dichroism (ECD) and 13C NMR calculations. New streptothiazolidine A (1) and streptodiketopiperazines A (2) and B (3) showed antifungal activity against Candida albicans with MIC values of 47, 42, and 42 g/mL, respectively.
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McGinty, D., C. S. Letizia et A. M. Api. « Fragrance material review on 1,2-ethanediol, 1-phenyl-, 1,2-diacetate ». Food and Chemical Toxicology 50 (septembre 2012) : S327—S329. http://dx.doi.org/10.1016/j.fct.2012.02.048.

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Yamagiwa, Kiyofumi, Yuriko Iwao, Masafumi Mikami, Tsuneharu Takeuchi, Morihiro Saito et Jun Kuwano. « Liquid-Phase Synthesis of Carbon Nanotubes from Alcohols ». Key Engineering Materials 350 (octobre 2007) : 19–22. http://dx.doi.org/10.4028/www.scientific.net/kem.350.19.

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Vertically aligned carbon nanotubes (CNTs) were grown on a stainless steel substrate (SUS304) by resistance-heating method in alcohols containing homogeneously dissolved cobaltocene Co(C5H5)2 as a catalyst source. Straight-chain primary alcohols, 1,2-ethanediol and cyclohexanol were used as carbon sources to examine the effects of the molecular structures on the morphology of the aligned CNTs. Methanol brought the best purity and alignment of CNTs of all the alcohols. The CNTs from 1,2-ethanediol was worse in the purity than those from ethanol with the same number of carbon atoms. The CNTs from cyclohexanol had a better purity than those from 1-hexanol. Distinctive features of this method are simple, low cost and a one-step process involving none of vacuum processes and catalyst preparation processes.
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Yang, Yun-Xu, et Shi-Xiang Liu. « Asymmetric-Catalysed Preparation and Stereochemistry of (R,R)-,(S,R)-(6-Fluoro-2-Chromanyl)-1,2-Ethanediol ». Journal of Chemical Research 2007, no 9 (septembre 2007) : 506–8. http://dx.doi.org/10.3184/030823407x240908.

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(R,R)-,(S,R)-1-(6-fluoro-2-chromanyl)-1,2-ethanediol 1a/1b were prepared by hydrolytic kinetic resolution (HKR) of terminal racemic epoxides using (R,R)-SalenCo(OAc) as a catalyst. Their configurations were established by comparison with two authentic samples by HPLC.
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Marx, Melissa A., Zhihao Cui, Sung Gu Cho, Benjamin P. Charnay et Anne C. Co. « (Keynote) Insights into the CO2 Reduction Pathway through the Electrolysis of Aldehydes ». ECS Meeting Abstracts MA2022-01, no 49 (7 juillet 2022) : 2093. http://dx.doi.org/10.1149/ma2022-01492093mtgabs.

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Investigating the electrochemical reduction of aldehydes to alcohols provides insights into the mechanistic pathways of converting CO2 to alcohols electrochemically. Both acetaldehyde and propionaldehyde were electrochemically reduced on a polycrystalline Cu catalyst to illustrate that it is a viable pathway to ethanol and 1-propanol, respectively, supporting the mechanistic route previously proposed in the literature. 13C and 1H NMR analysis on isotopically labeled acetaldehyde was utilized to trace the reduction process. In an aqueous solution, acetaldehyde is at equilibrium with ethanediol, and propionaldehyde with propanediol. The dissociation of adsorbed ethanediol to acetaldehyde and water was also found to be favorable on both Cu and Au surfaces. Experimental observations were also supported with DFT calculations, indicating a higher-energy reaction intermediate on Au (111) over Cu (100). In summary, the results from this study support previously proposed mechanisms and provide a framework for testing other stable CO2 reaction intermediates to gain insights into the overall CO2 reaction pathway. Figure 1
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Anosova, Galyna A., Vladislava V. Matveevskaya, Nurgul A. Pirmanova et Andrei S. Potapov. « Synthesis and Characterization of Transition Metal Complexes of 1,2-Bis(3,5-Dimethylpyrazol-1-yl)-1,2-Ethanediol ». Key Engineering Materials 685 (février 2016) : 754–58. http://dx.doi.org/10.4028/www.scientific.net/kem.685.754.

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Copper (II), nickel (II) and vanadyl complexes of 1,2-bis (3,5-dimethylpyrazol-1-yl)-1,2-ethanediol were prepared by the reaction of transition metal salts (chloride, acetate, sulfate) with the ligand in ethanol solution. The composition of the complexes was confirmed by elemental analysis and molar conductivity measurements. The coordination modes of the ligand and counter-ions were established from IR spectra and DFT calculations.
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12

Nie, Yao, Yan Xu, Xiao Qing Mu, Hai Yan Wang, Ming Yang et Rong Xiao. « Purification, Characterization, Gene Cloning, and Expression of a Novel Alcohol Dehydrogenase with Anti-Prelog Stereospecificity from Candida parapsilosis ». Applied and Environmental Microbiology 73, no 11 (13 avril 2007) : 3759–64. http://dx.doi.org/10.1128/aem.02185-06.

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ABSTRACT An alcohol dehydrogenase from Candida parapsilosis CCTCC M203011 was characterized along with its biochemical activity and structural gene. The amino acid sequence shows similarity to those of the short-chain dehydrogenase/reductases but no overall identity to known proteins. This enzyme with unusual stereospecificity catalyzes an anti-Prelog reduction of 2-hydroxyacetophenone to (S)-1-phenyl-1,2-ethanediol.
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13

Jie, Xia, Huang Xupei, R. Sreekumar et Jeffery W. Walker. « PHOTOLABILE ‘CAGED’ FATTY ACIDS CONTAINING A 1-(2′-NITROPHENYL)-1,2-ETHANEDIOL MOIETY ». Bioorganic & ; Medicinal Chemistry Letters 7, no 10 (mai 1997) : 1243–48. http://dx.doi.org/10.1016/s0960-894x(97)00199-6.

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Bikas, Rahman, Marzieh Emami et Anna Kozakiewicz. « Investigation of intermolecular interactions in the crystal structure of 1-phenyl-1,2-ethanediol ». Iranian Journal of Crystallography and Mineralogy 27, no 4 (1 décembre 2019) : 959–66. http://dx.doi.org/10.29252/ijcm.27.4.959.

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Wang, Nai-Xing, An-Guang Yu, Ya-Lan Xing, Jun-Ping Zhang, Yun-Xu Yang, Wu-Wei Wang et Rui-long Sheng. « A Convenient Synthesis of 1-[6-Fluoro-(2S)-3H,4H-dihydro-2H-2-chromenyl]-(1R)-1,2-ethanediol and 1-[6-Fluoro-(2R)-3H,4H-dihydro- 2H-2-chromenyl]-(1R)-1,2-ethanediol ». Synlett, no 9 (2005) : 1465–67. http://dx.doi.org/10.1055/s-2005-868508.

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Zhang, Rongzhen, Yan Xu, Rong Xiao, Lei Wang et Botao Zhang. « Optimized expression of (S)-carbonyl reductase inPichia pastorisfor efficient production of (S)-1-phenyl-1, 2-ethanediol ». Journal of Basic Microbiology 54, no 8 (17 juillet 2013) : 873–79. http://dx.doi.org/10.1002/jobm.201200780.

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Oda, Shinobu, Yutaka Kikuchi et Yasushi Nanishi. « Synthesis of Optically Active Mandelic AcidviaMicrobial Oxidation of Racemic 1-Phenyl-l,2-ethanediol ». Bioscience, Biotechnology, and Biochemistry 56, no 8 (janvier 1992) : 1216–20. http://dx.doi.org/10.1271/bbb.56.1216.

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Rani, M., K. Tariq, A. Younus, K. Batool, M. Sattar, R. Shafique, M. Bukhari, N. Akhtar et A. Mehmood. « Sol-gel Synthesis of Nanoscaled Spinels using 1, 2-ethanediol as a Gelation Agent ». Journal of Optoelectronic and Biomedical Materials 13, no 3 (juillet 2021) : 89–94. http://dx.doi.org/10.15251/jobm.2021.133.89.

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In the present work sodium chromite (NaCr2O4) based pigment was synthesized using sol gel technique. From XRD analysis, it is clear that all samples manufactured by sol gel technique have spinel structure crystallization. Also chromites with a chromium concentration (max) shows black color and Na- substituted shows green color. The samples were annealed at different temperature from 600˚C to 700˚C. The obtained nano particles were characterized by other different techniques as well such as Scanning electron microscopy, Raman spectroscopy, Photoluminence and Energy dispersive spectroscopy. The particle size of parent compound is ranging from 4.4nm to 11nm determined from SEM. The tendency of particles to form the aggregates with the increasing annealing temperature has been observed. The optical characterization of the compound shows that the sol gel attained material is strongly persuasive sodium chromite.
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Liu, Huan, Xianbao Cui, Ying Zhang, Tianyang Feng et Zhen Yang. « Isobaric vapor–liquid equilibrium of ethanenitrile + water + 1,2-ethanediol + 1-ethyl-3-methylimidazolium chloride ». Fluid Phase Equilibria 378 (septembre 2014) : 13–20. http://dx.doi.org/10.1016/j.fluid.2014.06.025.

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Zorębski, Edward. « Ultrasonic Absorption in Mixtures of 1,2-Ethanediol with 1-Nonanol at T = 298.15 K ». International Journal of Thermophysics 31, no 1 (20 octobre 2009) : 143–49. http://dx.doi.org/10.1007/s10765-009-0658-3.

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XIA, J., X. HUANG, R. SREEKUMAR et J. W. WALKER. « ChemInform Abstract : Photolabile “Caged” Fatty Acids Containing a 1-(2′-Nitrophenyl)-1,2- ethanediol Moiety. » ChemInform 28, no 39 (3 août 2010) : no. http://dx.doi.org/10.1002/chin.199739084.

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Nie, Yao, Yan Xu, Teng Fei Lv et Rong Xiao. « Enhancement ofCandida parapsilosiscatalyzing deracemization of (R,S)-1-phenyl-1, 2-ethanediol : agitation speed control during cell cultivation ». Journal of Chemical Technology & ; Biotechnology 84, no 3 (mars 2009) : 468–72. http://dx.doi.org/10.1002/jctb.2070.

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Tian, Xin, Gao-Wei Zheng, Chun-Xiu Li, Zhi-Long Wang et Jian-He Xu. « Enantioselective production of (S)-1-phenyl-1,2-ethanediol from dicarboxyesters by recombinant Bacillus subtilis esterase ». Journal of Molecular Catalysis B : Enzymatic 73, no 1-4 (décembre 2011) : 80–84. http://dx.doi.org/10.1016/j.molcatb.2011.07.022.

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Yang, Hong Lin, Wei Xiang et Guang Jie Chen. « Study on Preparation and Property of Regenerated Liquid Reactive Dyes Regenerated Magenta ». Advanced Materials Research 941-944 (juin 2014) : 445–49. http://dx.doi.org/10.4028/www.scientific.net/amr.941-944.445.

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The regenerated liquid reactive dye Regenerated Magenta had been prepared with the waste reactive ink of Jettex R Magenta in the process of digital inkjet printing. The effects of quality percentage of waste ink, cosolvent, pH regulator on the stabilities of Regenerated Magenta had been investigated. The results show that the Regenerated Magenta ink prepared with waste ink 26%, N-methyl-2-pyrrolidone 4%, THAM 1%, ethanediol 3% and deionized water 67% has good performances such as particle sizes, surface tension, viscosity and conductivity. The characteristics of Regenerated Magenta ink meet the demands of the ink for digital inkjet printing.
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Hall, Christopher, et Victoria Pugsley. « Spontaneous Capillary Imbibition of Water and Nonaqueous Liquids into Dry Quarry Limestones ». Transport in Porous Media 135, no 3 (2 novembre 2020) : 619–31. http://dx.doi.org/10.1007/s11242-020-01489-8.

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AbstractRates of spontaneous imbibition of water and nonaqueous liquids into dry limestones have been measured at 25 °C. Thirteen English and French limestones were used, with eight liquids (water, decane, dodecane, sec-butanol, iso-propanol, tetrahydrofuran, perfluorodimethylcyclohexane, ethanediol). For the nonaqueous liquids, the measured sorptivity generally scales as (surface-tension/viscosity)$$^{1/2}$$ 1 / 2 (here called F-scaling). Water sorptivities deviate from F-scaling, indicating partial wetting. A wetting coefficient (wetting index) is derived. Data show that there is little difference in the Hirschwald saturation coefficient measured with the different liquids, although there is a large variation between stones. Results suggest that physicochemical alteration of exposed pore surfaces strongly (and unpredictably) influences the capillary absorption of water by limestones.
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Zorębski, Edward, et Beata Lubowiecka-Kostka. « Thermodynamic and transport properties of (1,2-ethanediol+1-nonanol) at temperatures from (298.15 to 313.15)K ». Journal of Chemical Thermodynamics 41, no 2 (février 2009) : 197–204. http://dx.doi.org/10.1016/j.jct.2008.09.018.

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Liese, Andreas, Martin Karutz, Johan Kamphuis, Christian Wandrey et Udo Kragl. « Enzymatic resolution of 1-phenyl-1,2-ethanediol by enantioselective oxidation : Overcoming product inhibition by continuous extraction ». Biotechnology and Bioengineering 51, no 5 (26 mars 2000) : 544–50. http://dx.doi.org/10.1002/(sici)1097-0290(19960905)51:5<544 ::aid-bit6>3.0.co;2-c.

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Peng, F., X. ‐Y Ou, Y. Zhao, M. ‐H Zong et W. ‐Y Lou. « Highly selective resolution of racemic 1‐phenyl‐1,2‐ethanediol by a novel strain Kurthia gibsonii SC 0312 ». Letters in Applied Microbiology 68, no 5 (19 mars 2019) : 446–54. http://dx.doi.org/10.1111/lam.13123.

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Shokouhi, Mohammad, Ali Reza Rezaierad, Seyed-Majid Zekordi, Maryam Abbasghorbani et Mehdi Vahidi. « Solubility of Hydrogen Sulfide in Ethanediol, 1,2-Propanediol, 1-Propanol, and 2-Propanol : Experimental Measurement and Modeling ». Journal of Chemical & ; Engineering Data 61, no 1 (17 décembre 2015) : 512–24. http://dx.doi.org/10.1021/acs.jced.5b00680.

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Manjarrez, Alvarez, Méndez Pérez, Oba Solís, Cabello Ortega, Carvajal Lara, Ledezma Valencia et Rubria Martínez-Casares. « Application of the redox system of Nocardia corallina B-276 in the enantioselective biotransformation of ketones and alcohols ». Journal of the Serbian Chemical Society 85, no 3 (2020) : 279–90. http://dx.doi.org/10.2298/jsc180806089m.

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The aim of this research was to evaluate the redox system of Nocardia corallina B-276 in the biotransformation of 1-phenyl-1-propanone (1a), 2-hydroxy-1-phenylethanone (2a) and methyl (2-chlorophenyl)(oxo)acetate (3a) into 1-phenylpropan-1-ol (1b), 1-phenyl-1,2-ethanediol (2b) and methyl (2-chlorophenyl)(hydroxy)acetate (3b). The biomass of N. corallina was obtained in a liquid medium with an initial pH of 8.50, but the pH changed during the 96 h of the culture media, the final pH was between 4.74 and 7.62. The N. corallina biomass biocatalyzed the enantioselective reduction of 1a?3a to the corresponding alcohols. Whereas, during the process of oxidation of the rac-alcohols 1b?3b, 1b was oxidized in enantioselective way, the oxidation of 2b was not selective, but 3b was biotransformed mainly to (R)-3b. These results are indicative that N. corallina produced reductases and oxidases, whereby the biocatalytic activity was influenced by the final pH of the culture media, the reaction time and structure of the substrate.
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James, E. R., et R. Peacock. « Studies on the cryopreservation of Dictyocaulus viviparus (Nematoda) third-stage larvae ». Journal of Helminthology 60, no 1 (mars 1986) : 65–73. http://dx.doi.org/10.1017/s0022149x00008269.

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AbstractVarious cooling (01–5.100 Cmin−1) and warming (2O–6,8OO½Cmin−1) rates, stepped cooling schedules and four cryoprotective additives (dimethyl sulphoxide, methanol, ethanediol and glycerol) were investigated in cryopreservation studies with Dictyocaulus viviparus third-stage larvae. Exsheathment with sodium hypochlorite was essential to achieve significant survival. With uninterrupted cooling, highest survival (30% normally motile) was achieved with rates of 10–70½C min−1. Survival was higher (50–75%) using 1 ½C min−1 to — 10½C followed by plunging into liquid nitrogen. The optimum warming rate was 6,8OO½C min−1. The use of cryoprotectants led to marginally lower survival while varying the suspending media had no significant effect on survival. X-irradiated, exsheathed third-stage larvae cryopreserved by the optimum protocol yielded 38–3 ±4–2% survival. Two calves each infected with 45,000 (15,000 viable) exsheathed, unirradiated, C“ryopreserved third-stage larvae harboured 494 worms (11% infectivity) and 355 worms (0-8%) at necropsy. Numbers of first-stage larvae in the faeces reached 420/G and 105/G respectively 27 days after infection.
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Zorȩbski, Edward, et Anna Kulig. « Densities, Speeds of Sound, and Isentropic Compressibilities for Binary Mixtures of 1,2-Ethanediol with 2-Ethyl-1-hexanol, 1-Heptanol, or Ethanol at the Temperature 298.15 K and Densities for Mixtures of 1,2-Ethanediol with 1-Nonanol at the Temperatures (293.15 and 298.15) K ». Journal of Chemical & ; Engineering Data 55, no 9 (9 septembre 2010) : 3937–41. http://dx.doi.org/10.1021/je9010882.

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Jiménez, E., M. Cabanas, L. Segade, S. Garcı́a-Garabal et H. Casas. « Excess volume, changes of refractive index and surface tension of binary 1,2-ethanediol + 1-propanol or 1-butanol mixtures at several temperatures ». Fluid Phase Equilibria 180, no 1-2 (avril 2001) : 151–64. http://dx.doi.org/10.1016/s0378-3812(00)00519-7.

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Wang, Shanshan, Yao Nie, Xu Yan, Tzu-Ping Ko, Chun-Hsiang Huang, Hsiu-Chien Chan, Rey-Ting Guo et Rong Xiao. « Crystallization and preliminary X-ray diffraction analysis of (R)-carbonyl reductase fromCandida parapsilosis ». Acta Crystallographica Section F Structural Biology Communications 70, no 6 (24 mai 2014) : 800–802. http://dx.doi.org/10.1107/s2053230x1400908x.

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The NADH-dependent (R)-carbonyl reductase fromCandida parapsilosis(RCR) catalyzes the asymmetric reduction of 2-hydroxyacetophenone (HAP) to produce (R)-1-phenyl-1,2-ethanediol [(R)-PED], which is used as a versatile building block for the synthesis of pharmaceuticals and fine chemicals. To gain insight into the catalytic mechanism, the structures of complexes of RCR with ligands, including the coenzyme, are important. Here, the recombinant RCR protein was expressed and purified inEscherichia coliand was crystallized in the presence of NAD+. The crystals, which belonged to the orthorhombic space groupP212121, with unit-cell parametersa= 85.64,b= 106.11,c= 145.55 Å, were obtained by the sitting-drop vapour-diffusion method and diffracted to 2.15 Å resolution. Initial model building indicates that RCR forms a homotetramer, consistent with previous reports of medium-chain-type alcohol dehydrogenases.
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SHIRAI, HIROFUSA, SHUN-ICHI KONDO, KAZUMI NISHIHATA, ETSUKO ADACHI, MASAHIRO SUZUKI, SHINJI UCHIDA, MUTSUMI KIMURA, TOSHIKI KOYAMA et KENJI HANABUSA. « Functional Metallomacrocycles and Their Polymers 36 : Synthesis and Properties of Polyester Containing a Metallophthalocyanine Ring ». Journal of Porphyrins and Phthalocyanines 02, no 01 (janvier 1998) : 31–38. http://dx.doi.org/10.1002/(sici)1099-1409(199801/02)2:1<31 ::aid-jpp47>3.0.co;2-d.

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A novel class of copolyesters containing the metallophthalocyanine ring [ M - Pc , M = Fe ( III ), Co ( II )] in the chain was synthesized by polycondensation of (dicarboxyphthalocyaninato) metal [ M - Dapc , M = Fe ( III ), Co ( II )] diacid chloride, terephthalic acid chloride and aliphatic diols. The structures of the copolyesters were characterized by infrared, electronic as well as ESR spectra, and viscosity measurement. The thermal stabilities of the polymers were evaluated by dynamic thermogravimetric analyses. The polymers obtained thus were easily soluble in chloroform, dichloromethane, etc. The green or blue colored fiber was formed by melt spinning of the copolyesters containing below 1 mol % M - Pc component. The copolyester containing Co ( II )- Pc in the chain obtained from 1,2-ethanediol as a diol component catalysed the autoxidation of 2-mercaptoethanol in the presence of oxygen.
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Zhou, Xiaotian, Rongzhen Zhang, Yan Xu, Hongbo Liang, Jiawei Jiang et Rong Xiao. « Coupled (R)-carbonyl reductase and glucose dehydrogenase catalyzes (R)-1-phenyl-1,2-ethanediol biosynthesis with excellent stereochemical selectivity ». Process Biochemistry 50, no 11 (novembre 2015) : 1807–13. http://dx.doi.org/10.1016/j.procbio.2015.08.002.

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37

Marinas, Alberto, Tamas Mallat et Alfons Baiker. « 1-Naphthyl-1,2-ethanediol as a new chiral modifier of platinum in the enantioselective hydrogenation of activated ketones ». Journal of Catalysis 221, no 2 (25 janvier 2004) : 666–69. http://dx.doi.org/10.1016/j.jcat.2003.10.008.

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Wang, Rui, Xingang Li, Jian Na, Yan Wu, Runnan Zhao, Yutao Yan, Hong Li et Xin Gao. « Reversible reaction-assisted intensification process for separating ethanediol and 1, 2-butanediol : Competitive kinetics study and conceptual design ». Separation and Purification Technology 237 (avril 2020) : 116323. http://dx.doi.org/10.1016/j.seppur.2019.116323.

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Chen, Xi, Ting Mei, Yunfeng Cui, Qijia Chen, Xiangtao Liu, Jinhui Feng, Qiaqing Wu et Dunming Zhu. « Highly Efficient Synthesis of Optically Pure (S )-1-phenyl-1,2-ethanediol by a Self-Sufficient Whole Cell Biocatalyst ». ChemistryOpen 4, no 4 (30 avril 2015) : 483–88. http://dx.doi.org/10.1002/open.201500045.

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Mu, Xiao Qing, Yan Xu, Yao Nie, Jian Ouyang et Zhi Hao Sun. « Candida parapsilosis CCTCC M203011 and the optimization of fermentation medium for stereoinversion of (S)-1-phenyl-1,2-ethanediol ». Process Biochemistry 40, no 7 (juin 2005) : 2345–50. http://dx.doi.org/10.1016/j.procbio.2004.09.026.

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Zhang, Rongzhen, Yan Xu, Rong Xiao, Shanshan Wang et Botao Zhang. « Improved production of (R)-1-phenyl-1,2-ethanediol using Candida parapsilosis (R)-carbonyl reductase expressed in Pichia pastoris ». Process Biochemistry 46, no 3 (mars 2011) : 709–13. http://dx.doi.org/10.1016/j.procbio.2010.11.016.

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Chen, Guang-Ming, et P. Veeraraghavan Ramachandran. « Efficient syntheses of enantiomerically pure 1,2-dicyclohexenyl- and 1,2-dicyclohexyl-1,2-ethanediol using B-2-cyclohexen-1-yl-diisopinocampheylborane ». Tetrahedron : Asymmetry 8, no 23 (décembre 1997) : 3935–38. http://dx.doi.org/10.1016/s0957-4166(97)00567-3.

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43

Tatham, A. S., A. F. Drake et P. R. Shewry. « Conformational studies of a synthetic peptide corresponding to the repeat motif of C hordein ». Biochemical Journal 259, no 2 (15 avril 1989) : 471–76. http://dx.doi.org/10.1042/bj2590471.

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C hordein, a storage protein from barley grains, has an Mr of about 53,000, and consists predominantly of repeated octapeptides with a consensus sequence of Pro-Gln-Gln-Pro-Phe-Pro-Gln-Gln. Previously reported hydrodynamic and c.d. studies indicate the presence of beta-turns, the repetitive nature of which may lead to the formation of a loose spiral. In order to study these turns we have compared the structures of a synthetic peptide corresponding to the consensus repeat motif and total C hordein by using c.d. and Fourier-transform i.r. spectroscopy. The synthetic peptide exhibited spectra typical of beta I/III reverse turns when dissolved in trifluoroethanol at 22 degrees C and in water at 70 degrees C, but ‘random-coil’-like spectra in water at 22 degrees C. The whole protein also showed increases in beta I/III reverse turns when dissolved in increasing concentrations of trifluoroethanol (50-100%, v/v) or heated in ethanol/water (7:3, v/v). Two cryogenic solvent systems were used to determine the c.d. spectra of the peptide and protein at temperatures down to -100 degrees C. Methanol/glycerol (9:1, v/v) and ethanediol/water (2:1, v/v) were selected as analogues of trifluoroethanol/water and water respectively. The peptide exhibited beta I/III-reverse-turn and ‘random-coil’-like spectra in methanol/glycerol and ethanediol/water respectively at 22 degrees C, but a spectrum similar to that of a poly-L-proline II helix in both solvents at -100 degrees C. Similarly the proportion of this spectral type also increased when the whole protein was cooled in both solvents. These results indicate that a poly-L-proline II conformation at low temperatures is in equilibrium with a beta I/III-turn-rich conformation at higher temperatures. The latter conformation is also favoured in solvents of low dielectric constant such as trifluoroethanol. The ‘random-coil‘-like spectra exhibited by the protein and peptide in high-dielectric-constant solvents at room temperature may result from a mixture of the two conformations rather than from the random-coil state.
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Amarasekara, Ananda S., et Rocio Garcia-Obregon. « Vanillin based polymers : V. Poly(hydrovanilloin–urethane) ». Polymers from Renewable Resources 12, no 1-2 (février 2021) : 35–45. http://dx.doi.org/10.1177/2041247921989898.

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Renewable resources based hydrovanilloin [1,2- bis(4-hydroxy-3-methoxyphenyl)-1,2-ethanediol] was synthesized in 86% yield by electrochemical dimerization of vanillin in aqueous NaOH. This symmetrical bis-phenol monomer was then used for the preparation of urethane polymers by two different methods. In the first method a 1:2 mole ratio mixture of hydrovanilloin and diisocyanate was polymerized in DMF using 1,4-diazabicyclo[2,2,2]octane as the catalyst at 60°C, for 1 h to give poly(hydrovanilloin–urethane)s. In the second method diisocyanates were first reacted with polyethylene glycol-400 to give pre-polymers. Then prepolymers were reacted with equivalent amount of hydrovanilloin at 60°C for 4 days to produce poly(hydrovanilloin-ethylene glycol-urethane)s. The first method resulted hard poly(hydrovanilloin–urethane)s showing Tg values in the range of 121–172°C. The second method yielded softer poly(hydrovanilloin-ethylene glycol-urethane)s and these polymers failed to show distinct glass transition temperatures in the DSC analysis. However, poly(hydrovanilloin-ethylene glycol-urethane)s showed better thermal stabilities than polymers without polyethylene glycol units.
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VELASCO B., Rodrigo, Jesús H. GIL G., Carlos M. GARCÍA P. et Diego L. DURANGO R. « PRODUCTION OF 2-PHENYLETHANOL IN THE BIOTRANSFORMATION OF CINNAMYL ALCOHOL BY THE PLANT PATHOGENIC FUNGUS <I>Colletotrichum acutatum</I> ; ». Vitae 17, no 3 (9 novembre 2010) : 272–80. http://dx.doi.org/10.17533/udea.vitae.7434.

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Biocatalytic processes may offer a cheaper alternative to natural production of flavours. The biotransformation of cinnamyl alcohol is investigated using the plant pathogenic fungus Colletotrichum acutatum as a biocatalyst. Results show that substrate is converted to 3-phenyl-1-propanol, 1-phenyl-1,3- propanediol, 2-phenylethanol, 1-phenyl-1,2-ethanediol, 3-phenyl propyl acetate, and hydrocinnamic acid. The structures of the metabolic products are elucidated on the basis of their spectral data. 2-phenylethanol has a sweet, floral odor and a wide variety of applications, especially, for the perfume and food industries. A time-course experiment demonstrates that 2-phenylethanol appeared after 120 hours, reaching almost 8% of relative abundance. Additionally, the influence that the culture broth has on the conversion capacity is investigated. It has been discovered that cinnamyl alcohol is converted faster when the substrate is incorporated in a Sabouraud medium; under this condition, 2-phenylethanol is the most common product after 288 hours reaching about 90% of the relative abundance. Biotransformation of cinnamyl alcohol using C. acutatum in a Sabouraud medium can offer a simple and efficient way to obtain 2-phenylethanol with high yield.
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Geng, Yawei, Rongzhen Zhang, Yan Xu, Shanshan Wang, Chong Sha et Rong Xiao. « Coexpression of a carbonyl reductase and glucose 6-phosphate dehydrogenase inPichia pastorisimproves the production of (S)-1-phenyl-1,2-ethanediol ». Biocatalysis and Biotransformation 29, no 5 (22 septembre 2011) : 172–78. http://dx.doi.org/10.3109/10242422.2011.594881.

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Mamidi, Rao N. V. S., Geert Mannens, Pieter Annaert, Jan Hendrickx, Ivo Goris, Mark Bockx, Cor G. M. Janssen, Mark Kao, Michael F. Kelley et Willem Meuldermans. « Metabolism and Excretion of RWJ-333369 [1,2-Ethanediol, 1-(2-Chlorophenyl)-, 2-carbamate, (S)-] in Mice, Rats, Rabbits, and Dogs ». Drug Metabolism and Disposition 35, no 4 (12 janvier 2007) : 566–75. http://dx.doi.org/10.1124/dmd.106.012336.

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Marinas, Alberto, Tamas Mallat et Alfons Baiker. « Erratum to “1-Naphthyl-1,2-ethanediol as a new chiral modifier of platinum in the enantioselective hydrogenation of activated ketones” ». Journal of Catalysis 223, no 2 (avril 2004) : 466. http://dx.doi.org/10.1016/j.jcat.2004.03.012.

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Nie, Yao, Yan Xu et Xiao Qing Mu. « Highly Enantioselective Conversion of Racemic 1-Phenyl-1,2-ethanediol by Stereoinversion Involving a Novel Cofactor-Dependent Oxidoreduction System ofCandidaparapsilosisCCTCC M203011 ». Organic Process Research & ; Development 8, no 2 (mars 2004) : 246–51. http://dx.doi.org/10.1021/op0341519.

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Zhang, Rongzhen, Yawei Geng, Yan Xu, Wenchi Zhang, Shanshan Wang et Rong Xiao. « Carbonyl reductase SCRII from Candida parapsilosis catalyzes anti-Prelog reaction to (S)-1-phenyl-1,2-ethanediol with absolute stereochemical selectivity ». Bioresource Technology 102, no 2 (janvier 2011) : 483–89. http://dx.doi.org/10.1016/j.biortech.2010.08.060.

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