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Carbohydrate Chemistry. Chemical and Biological Approaches
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SYSNO ASEP 0354023 Document Type M - Monograph Chapter R&D Document Type Monograph Chapter Title Azido leaving group in enzymatic synthesis-small and efficient Author(s) Bojarová, Pavla (MBU-M) ORCID
Křen, Vladimír (MBU-M) RID, ORCIDSource Title Carbohydrate Chemistry. Chemical and Biological Approaches. - Thomas Graham House, Science Park, Milton Road : The Royal Society of Chemistry, 2010 / Rauter A. P. ; Lindhorst K. T. - ISBN 9781847550446 Pages s. 168-175 Number of pages 6 s. Number of copy 1300 Number of pages 193 Language eng - English Country GB - United Kingdom Keywords carbohydrate synthesis ; glycoside donors ; glycosyl azides Subject RIV CC - Organic Chemistry R&D Projects OC08049 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) DOI - Annotation Enzymatic transglycosylation catalyzed by glycosidases is a respected method in carbohydrate synthesis. The spectrum of acceptors is practically infinite, contrary to glycosyl donors, which are usually nitrophenyl glycosides. Their major advantage is good reactivity, however, their low water solubility causes lower transglycosylation yields since high concentrations of substrates are needed to promote transglycosylation at the expense of donor hydrolysis. This is especially the case of modified glycoside donors where some OH groups are substituted with more lipophilic substituents. The solubility problems are generally incurred by hydrophobic leaving groups. Furthermore, commercial nitrophenyl glycosides are expensive and the yields of their syntheses may be unsatisfactory. Therefore, alternative glycosyl donors are emerging, such as 3-nitro- and 5-nitro-2-pyridyl glycosides, vinyl glycosides and glycosyl fluorides, which exhibit many properties common to glycosyl azides Workplace Institute of Microbiology Contact Eliška Spurná, eliska.spurna@biomed.cas.cz, Tel.: 241 062 231 Year of Publishing 2011
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