title: 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).
authors.affiliation: Department of Chemistry, University of British Columbia, Vancouver, BC, Canada V6T 1Z1.
authors.forename: Alain
authors.initials: A
authors.lastname: Mayer
authors.forename: Tracey M
authors.initials: TM
authors.lastname: Gloster
authors.forename: Wayne K
authors.initials: WK
authors.lastname: Chou
authors.forename: David J
authors.initials: DJ
authors.lastname: Vocadlo
authors.forename: Martin E
authors.initials: ME
authors.lastname: Tanner
mesh_terms: D001386:Azides / Q000138:chemical synthesis / Q000737:chemistry; D006801:Humans; D008562:Membrane Glycoproteins / Q000737:chemistry / Q000378:metabolism; D017351:N-Acetylglucosaminyltransferases / Q000737:chemistry* / Q000378:metabolism; D028861:Nuclear Pore Complex Proteins / Q000737:chemistry / Q000378:metabolism; D013379:Substrate Specificity; D014537:Uridine Diphosphate N-Acetylglucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001386:Azides; D008562:Membrane Glycoproteins; D028861:Nuclear Pore Complex Proteins; C049312:nuclear pore protein p62; D014537:Uridine Diphosphate N-Acetylglucosamine; D017351:N-Acetylglucosaminyltransferases; C063057:UDP-N-acetylglucosamine-peptide beta-N-acetylglucosaminyltransferase