Solid-phase oligosaccharide and glycopeptide synthesis using glycosynthases.

Jakob F Tolborg; Lars Petersen; Knud J Jensen; Christoph Mayer; David L Jakeman; R Antony J Warren; Stephen G Withers

doi:10.1021/jo0163445

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Solid-phase oligosaccharide and glycopeptide synthesis using glycosynthases.

Jakob F Tolborg·Lars Petersen·Knud J Jensen·Christoph Mayer·David L Jakeman·R Antony J Warren·Stephen G Withers

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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, alpha-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.

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Acetylation Amination Amino Acid Sequence Chromatography, High Pressure Liquid Glycine Glycopeptides Glycosylation Magnetic Resonance Spectroscopy Models, Molecular Molecular Structure Mutation Oligosaccharides Peptides Resins, Plant Rhizobium Serine beta-Glucosidase Journal Article Research Support, Non-U.S. Gov't

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Jakob F Tolborg, Lars Petersen, Knud J Jensen, Christoph Mayer, David L Jakeman, R Antony J Warren, Stephen G Withers. 2002-06-14. Solid-phase oligosaccharide and glycopeptide synthesis using glycosynthases.. https://doi.org/10.1021/jo0163445

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