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

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

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.

    Research areas

  • 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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