Carbohydrate Chemistry. Chemical and Biological Approaches

0354023 - MBÚ 2011 RIV GB eng M - Monography Chapter
Bojarová, Pavla - Křen, Vladimír
Azido leaving group in enzymatic synthesis-small and efficient.
Carbohydrate Chemistry. Chemical and Biological Approaches. Thomas Graham House, Science Park, Milton Road: The Royal Society of Chemistry, 2010 - (Rauter, A.; Lindhorst, K.), s. 168-175. ISBN 9781847550446
R&D Projects: GA MŠMT OC08049
Keywords : carbohydrate synthesis * glycoside donors * glycosyl azides
Subject RIV: CC - Organic Chemistry

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
Permanent Link: http://hdl.handle.net/11104/0193115