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Neoglycorandomization and chemoenzymatic glycorandomization: two complementary tools for natural product

Joseph M Langenhan1, Byron R Griffith, Jon S Thorson

  • 1Laboratory for Biosynthetic Chemistry, Pharmaceutical Sciences Division, School of Pharmacy, University of Wisconsin-Madison, 777 Highland Avenue, Madison, Wisconsin 53705, USA.

Journal of Natural Products
|November 29, 2005
PubMed
Summary
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Chemists explore glycosylated natural products using novel glycorandomization methods. This review covers advances in monosaccharide generation and two key strategies: neoglycorandomization and chemoenzymatic glycorandomization.

Area of Science:

  • Natural Product Chemistry
  • Synthetic Chemistry
  • Biocatalysis

Background:

  • Glycosylated natural products are pharmaceutically important.
  • Understanding sugar contributions requires diverse analogues.
  • Current methods for analogue generation are limited.

Purpose of the Study:

  • To review recent advances in glycosylation strategies for natural products.
  • To highlight progress in neoglycorandomization and chemoenzymatic glycorandomization.
  • To discuss developments in monosaccharide generation for these methods.

Main Methods:

  • Neoglycorandomization: A one-step chemical ligation without sugar protection/activation.
  • Chemoenzymatic glycorandomization: A biocatalytic approach using enzyme promiscuity.

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  • Focus on methods requiring reducing sugars.

    • Main Results:

    • Recent advances in monosaccharide generation are presented.
    • Overview of progress in neoglycorandomization techniques.
    • Overview of progress in chemoenzymatic glycorandomization techniques.

    Conclusions:

    • Neoglycorandomization and chemoenzymatic glycorandomization offer powerful approaches for analogue library generation.
    • Advances in monosaccharide synthesis are crucial for these glycorandomization strategies.
    • These methods facilitate the exploration of structure-activity relationships in glycosylated natural products.