Neoglycorandomization and chemoenzymatic glycorandomization: Two complementary tools for natural product diversification

Joseph M. Langenhan, Byron R. Griffith, Jon S. Thorson

Research output: Contribution to journalArticlepeer-review

131 Scopus citations

Abstract

In an effort to explore the contribution of the sugar constituents of pharmaceutically relevant glycosylated natural products, chemists have developed glycosylation methods that are amenable to the generation of libraries of analogues with a broad array of glycosidic attachments. Recently, two complementary glycorandomization strategies have been described, namely, neoglycorandomization, a chemical approach based on a one-step sugar ligation reaction that does not require any prior sugar protection or activation, and chemoenzymatic glycorandomization, a biocatalytic approach that relies on the substrate promiscuity of enzymes to activate and attach sugars to natural products. Since both methods require reducing sugars, this review first highlights recent advances in monosaccharide generation and then follows with an overview of recent progress in the development of neoglycorandomization and chemoenzymatic glycorandomization.

Original languageEnglish
Pages (from-to)1696-1711
Number of pages16
JournalJournal of Natural Products
Volume68
Issue number11
DOIs
StatePublished - Nov 2005

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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