Solid-phase oligosaccharide and glycopeptide synthesis using glycosynthases

Jakob Fjord Tolborg, Lars Petersen, Knud Jørgen Jensen, C. Mayer, D.L. Jakeman, R.A.J. Warren, S.G. Withers

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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.
Original languageEnglish
JournalJournal of organic chemistry
Issue number12
Pages (from-to)4143-4149
Publication statusPublished - 2002


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