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

Department of Chemistry, University of British Columbia, Vancouver, BC, Canada V6T 1Z1.

Bioorganic & medicinal chemistry letters 2011 Feb 15

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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.

Citation

Alain Mayer, Tracey M Gloster, Wayne K Chou, David J Vocadlo, Martin E Tanner. 6''-Azido-6''-deoxy-UDP-N-acetylglucosamine as a glycosyltransferase substrate. Bioorganic & medicinal chemistry letters. 2011 Feb 15;21(4):1199-201