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

doi:10.1016/j.bmcl.2010.12.090

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

Research output: Contribution to journal › Article › peer-review

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 alpha-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). (c) 2011 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	1199-1201
Number of pages	3
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	21
Issue number	4
DOIs	https://doi.org/10.1016/j.bmcl.2010.12.090
Publication status	Published - 15 Feb 2011

Keywords

Glycosyltransferase
Azide
Sugar nucleotide
Click chemistry
UDP-N-acetylglucosamine
GLCNAC-MODIFIED PROTEINS
LINKED N-ACETYLGLUCOSAMINE
O-GLCNAC
NUCLEAR-PORE
STAUDINGER LIGATION
LIVING ANIMALS
CELL-SURFACES
IDENTIFICATION
GLYCOSYLATION
GLYCOPROTEINS

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@article{882740ea452c4e6dbb419cb2ed72d378,

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 alpha-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). (c) 2011 Elsevier Ltd. All rights reserved.",

keywords = "Glycosyltransferase, Azide, Sugar nucleotide, Click chemistry, UDP-N-acetylglucosamine, GLCNAC-MODIFIED PROTEINS, LINKED N-ACETYLGLUCOSAMINE, O-GLCNAC, NUCLEAR-PORE, STAUDINGER LIGATION, LIVING ANIMALS, CELL-SURFACES, IDENTIFICATION, GLYCOSYLATION, GLYCOPROTEINS",

author = "Alain Mayer and Gloster, {Tracey M.} and Chou, {Wayne K.} and Vocadlo, {David J.} and Tanner, {Martin E.}",

year = "2011",

month = feb,

day = "15",

doi = "10.1016/j.bmcl.2010.12.090",

language = "English",

volume = "21",

pages = "1199--1201",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier",

number = "4",

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TY - JOUR

T1 - 6 ''-Azido-6 ''-deoxy-UDP-N-acetylglucosamine as a glycosyltransferase substrate

AU - Mayer, Alain

AU - Gloster, Tracey M.

AU - Chou, Wayne K.

AU - Vocadlo, David J.

AU - Tanner, Martin E.

PY - 2011/2/15

Y1 - 2011/2/15

N2 - 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 alpha-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). (c) 2011 Elsevier Ltd. All rights reserved.

AB - 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 alpha-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). (c) 2011 Elsevier Ltd. All rights reserved.

KW - Glycosyltransferase

KW - Azide

KW - Sugar nucleotide

KW - Click chemistry

KW - UDP-N-acetylglucosamine

KW - GLCNAC-MODIFIED PROTEINS

KW - LINKED N-ACETYLGLUCOSAMINE

KW - O-GLCNAC

KW - NUCLEAR-PORE

KW - STAUDINGER LIGATION

KW - LIVING ANIMALS

KW - CELL-SURFACES

KW - IDENTIFICATION

KW - GLYCOSYLATION

KW - GLYCOPROTEINS

U2 - 10.1016/j.bmcl.2010.12.090

DO - 10.1016/j.bmcl.2010.12.090

M3 - Article

SN - 0960-894X

VL - 21

SP - 1199

EP - 1201

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 4

ER -

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

Abstract

Keywords

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