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Solid-phase oligosaccharide and glycopeptide synthesis using glycosynthases

TitleSolid-phase oligosaccharide and glycopeptide synthesis using glycosynthases
Publication TypeJournal Article
Year of Publication2002
AuthorsTolborg, JF, Petersen, L, Jensen, KJ, Mayer, C, Jakeman, DL, WARREN, RAJ, Withers, SG
JournalJOURNAL OF ORGANIC CHEMISTRY
Volume67
Pagination4143-4149
Date PublishedJUN 14
ISSN0022-3263
Abstract

Enzymatic approaches for the preparation of oligosaccharides are interesting alternatives to traditional chemical synthesis, the main advantage being the regio- and stereoselectivity offered without the need for protecting groups. The use of solid-phase techniques offers easy workup procedures and the prospect of automatability. Here, we report the first application of glycosynthases to solid-phase oligosaccharide synthesis by use of the 51 kDa serine and glycine mutants of Agrobacterium sp. beta-glucosidase, Abg E358S and E358G. Acceptors were linked to PEGA resin through a backbone amide linker (BAL), and using these mutated enzymes, a galactose moiety was transferred from a donor sugar, U-D-galactosyl fluoride, with high efficiency (>90%) together with excellent recovery of material. Furthermore, it was demonstrated that a resin-bound model glycopeptide was also an acceptor for the glycosynthase.

DOI10.1021/jo0163445