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

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).