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Solid-phase oligosaccharide and glycopeptide synthesis using glycosynthases.

Jakob F Tolborg1, Lars Petersen, Knud J Jensen

  • 1Department of Chemistry, Building 201, Kemitorvet, Technical University of Denmark, DK-2800, Kgs. Lyngby, Denmark.

The Journal of Organic Chemistry
|June 11, 2002
PubMed
Summary

This study introduces glycosynthases for solid-phase oligosaccharide synthesis, offering a highly efficient and selective enzymatic method. This approach simplifies the preparation of complex carbohydrates, including those found in glycopeptides.

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Area of Science:

  • Carbohydrate Chemistry
  • Enzymatic Synthesis
  • Glycobiology

Background:

  • Traditional chemical synthesis of oligosaccharides often requires protecting groups and lacks regio- and stereoselectivity.
  • Enzymatic synthesis offers a more selective and efficient alternative for oligosaccharide preparation.
  • Solid-phase techniques facilitate easier workup and potential automation in synthesis.

Purpose of the Study:

  • To report the first application of glycosynthases in solid-phase oligosaccharide synthesis.
  • To demonstrate the efficiency and selectivity of mutated Agrobacterium sp. beta-glucosidase (Abg E358S and E358G) in this process.
  • To explore the use of resin-bound acceptors, including model glycopeptides.

Main Methods:

  • Utilized serine (E358S) and glycine (E358G) mutants of Agrobacterium sp. beta-glucosidase (Abg) as glycosynthases.

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  • Linked acceptor molecules to PEGA resin via a backbone amide linker (BAL).
  • Transferred a galactose moiety from alpha-D-galactosyl fluoride to the resin-bound acceptor.

    • Main Results:

    • Achieved highly efficient transfer (>90%) of the galactose moiety using the mutated glycosynthases.
    • Demonstrated excellent recovery of the synthesized material.
    • Confirmed that resin-bound model glycopeptides can serve as acceptors for the glycosynthase.

    Conclusions:

    • Glycosynthases are effective tools for solid-phase oligosaccharide synthesis, providing regio- and stereoselectivity without protecting groups.
    • This enzymatic, solid-phase approach offers a promising route for efficient and automatable synthesis of complex carbohydrates.
    • The method is applicable to the synthesis of glycopeptide-related structures.