A simple strategy for glycosyltransferase-catalyzed aminosugar nucleotide synthesis

Jianjun Zhang, Shanteri Singh, Ryan R. Hughes, Maoquan Zhou, Manjula Sunkara, Andrew J. Morris, Jon S. Thorson

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

A set of 2-chloro-4-nitrophenyl glucosamino-/xylosaminosides were synthesized and assessed as potential substrates in the context of glycosyltransferase-catalyzed formation of the corresponding UDP/TDP-α-D-glucosamino-/xylosaminosugars and in single-vessel model transglycosylation reactions. This study highlights a robust platform for aminosugar nucleotide synthesis and reveals OleD Loki to be a proficient catalyst for U/TDP-aminosugar synthesis and utilization. 2-Chloro-4-nitrophenyl glucosamine-/xylosaminosides were synthesized and assessed as potential substrates for glycosyltransferase-catalyzed formation of the corresponding UDP/TDP-α-D-glucosamino-/xylosaminosugars and in single-vessel model transglycosylation reactions. This study highlights a robust platform for aminosugar nucleotide synthesis and reveals OleD Loki as a proficient catalyst for U/TDP-aminosugar synthesis.

Original languageEnglish
Pages (from-to)647-651
Number of pages5
JournalChemBioChem
Volume15
Issue number5
DOIs
StatePublished - Mar 21 2014

Keywords

  • carbohydrates
  • enzymes
  • glycobiology
  • glycorandomization
  • glycosides
  • glycosylation

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry

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