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New approaches to enzymatic oligosaccharide synthesis: Glycosynthases and thioglycoligases

TitleNew approaches to enzymatic oligosaccharide synthesis: Glycosynthases and thioglycoligases
Publication TypeJournal Article
Year of Publication2003
AuthorsJahn, M, Withers, SG
JournalBIOCATALYSIS AND BIOTRANSFORMATION
Volume21
Pagination159-166
Date PublishedAUG
ISSN1024-2422
Abstract

An overview of the applications of engineered glycosynthases and thioglycoligases for the enzymatic synthesis of O- and S-glycosidic linkages in oligosaccharides is presented. Glycosynthases lack the catalytic nucleophile of retaining glycosidases and use glycosyl fluorides with inverted anomeric stereochemistry as glycosyl donors. To date, nine enzymes from seven different glycosyl hydrolase families have been engineered to perform the glycosynthase reaction. Thioglycoligases lack the catalytic acid/base residue of retaining glycosidases and use dinitrophenyl glycosides as donors and deoxy-thiosugars as acceptors. The regioselectivity of the transglycosylation reaction is entirely controlled by the position of the thiol in the acceptor. To date, two retaining exo glycosidases and one endo glycanase, all from different glycosyl hydrolase families, have been engineered in this fashion.

DOI10.1080/1024220310001614351