6 ''-Azido-6 ''-deoxy-UDP-N-acetylglucosamine as a glycosyltransferase substrate

Alain Mayer, Tracey M. Gloster, Wayne K. Chou, David J. Vocadlo, Martin E. Tanner

Research output: Contribution to journalArticlepeer-review

Abstract

6 ''-Azido-6 ''-deoxy-UDP-N-acetylglucosamine (UDP-6Az-GlcNAc) is a potential alternate substrate for N-acetylglucosaminyltransferases. This compound could be used to generate various glycoconjugates bearing an azide functionality that could in turn be subjected to further modification using Staudinger ligation or Huisgen cycloaddition. UDP-6Az-GlcNAc is synthesized from alpha-benzyl-N-acetylglucosaminoside in seven-steps with an overall yield of 6%. It is demonstrated to serve as a substrate donor for the glycosyl transfer reaction catalyzed by the human UDP-GlcNAc:polypeptidyltransferase (OGT) to the acceptor protein nucleoporin 62 (nup62). (c) 2011 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)1199-1201
Number of pages3
JournalBioorganic & Medicinal Chemistry Letters
Volume21
Issue number4
DOIs
Publication statusPublished - 15 Feb 2011

Keywords

  • Glycosyltransferase
  • Azide
  • Sugar nucleotide
  • Click chemistry
  • UDP-N-acetylglucosamine
  • GLCNAC-MODIFIED PROTEINS
  • LINKED N-ACETYLGLUCOSAMINE
  • O-GLCNAC
  • NUCLEAR-PORE
  • STAUDINGER LIGATION
  • LIVING ANIMALS
  • CELL-SURFACES
  • IDENTIFICATION
  • GLYCOSYLATION
  • GLYCOPROTEINS

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