Chemoenzymatic synthesis of uridine 5'-diphospho-2-acetonyl-2-deoxy-alpha-D-glucose as C(2)-carbon isostere of UDP-GlcNAc

J Org Chem. 2010 May 21;75(10):3492-4. doi: 10.1021/jo100385p.

Abstract

2-ketoGlc, which is the C(2)-carbon isostere of GlcNAc, is a novel GlcNAc analogue with a ketone group. The corresponding glycosyltransferase donor substrate, UDP-2-ketoGlc, is necessary for synthesizing 2-ketoGlc-containing molecules and is thus highly important for metabolic polysaccharide remodeling and engineering. We report here the first chemoenzymatic synthesis of UDP-2-ketoGlc using our two-enzyme (NahK and GlmU) system in vitro.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocatalysis
  • Molecular Structure
  • Nucleotidyltransferases / chemistry
  • Nucleotidyltransferases / metabolism*
  • Phosphotransferases / chemistry
  • Phosphotransferases / metabolism*
  • Stereoisomerism
  • Uridine Diphosphate Glucose / analogs & derivatives*
  • Uridine Diphosphate Glucose / chemistry
  • Uridine Diphosphate Glucose / metabolism*
  • Uridine Diphosphate N-Acetylglucosamine / analogs & derivatives
  • Uridine Diphosphate N-Acetylglucosamine / chemistry*

Substances

  • Uridine Diphosphate N-Acetylglucosamine
  • Phosphotransferases
  • Nucleotidyltransferases
  • UDPacetylglucosamine pyrophosphorylase
  • Uridine Diphosphate Glucose