Bioorganic and Medicinal Chemistry Letters p. 1199 - 1201 (2011)
Update date:2022-09-26
Topics:
Mayer, Alain
Gloster, Tracey M.
Chou, Wayne K.
Vocadlo, David J.
Tanner, Martin E.
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).
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