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 α-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).
Copyright © 2011 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Azides / chemical synthesis
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Azides / chemistry
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Humans
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Membrane Glycoproteins / chemistry
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Membrane Glycoproteins / metabolism
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N-Acetylglucosaminyltransferases / chemistry*
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N-Acetylglucosaminyltransferases / metabolism
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Nuclear Pore Complex Proteins / chemistry
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Nuclear Pore Complex Proteins / metabolism
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Substrate Specificity
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Uridine Diphosphate N-Acetylglucosamine / analogs & derivatives*
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Uridine Diphosphate N-Acetylglucosamine / chemical synthesis
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Uridine Diphosphate N-Acetylglucosamine / chemistry
Substances
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Azides
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Membrane Glycoproteins
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Nuclear Pore Complex Proteins
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nuclear pore protein p62
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Uridine Diphosphate N-Acetylglucosamine
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N-Acetylglucosaminyltransferases
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UDP-N-acetylglucosamine-peptide beta-N-acetylglucosaminyltransferase