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Literature DB >> 21273069

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

Alain Mayer¹, Tracey M Gloster, Wayne K Chou, David J Vocadlo, Martin E Tanner.

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).

Entities: Chemical Gene Species

Mesh：

Substances：

Year: 2010 PMID： 21273069 DOI： 10.1016/j.bmcl.2010.12.090

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

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Cited

10 in total

1. The New Chemical Reporter 6-Alkynyl-6-deoxy-GlcNAc Reveals O-GlcNAc Modification of the Apoptotic Caspases That Can Block the Cleavage/Activation of Caspase-8.

Authors: Kelly N Chuh; Anna R Batt; Balyn W Zaro; Narek Darabedian; Nicholas P Marotta; Caroline K Brennan; Arya Amirhekmat; Matthew R Pratt
Journal: J Am Chem Soc Date: 2017-05-31 Impact factor: 15.419

2. Azide- and Alkyne-Bearing Metabolic Chemical Reporters of Glycosylation Show Structure-Dependent Feedback Inhibition of the Hexosamine Biosynthetic Pathway.

Authors: Lisa A Walter; Anna R Batt; Narek Darabedian; Balyn W Zaro; Matthew R Pratt
Journal: Chembiochem Date: 2018-08-10 Impact factor: 3.164

3. Metabolic Chemical Reporters of Glycans Exhibit Cell-Type-Selective Metabolism and Glycoprotein Labeling.

Authors: Anna R Batt; Balyn W Zaro; Marisol X Navarro; Matthew R Pratt
Journal: Chembiochem Date: 2017-03-28 Impact factor: 3.164

4. The Metabolic Chemical Reporter 6-Azido-6-deoxy-glucose Further Reveals the Substrate Promiscuity of O-GlcNAc Transferase and Catalyzes the Discovery of Intracellular Protein Modification by O-Glucose.

Authors: Narek Darabedian; Jinxu Gao; Kelly N Chuh; Christina M Woo; Matthew R Pratt
Journal: J Am Chem Soc Date: 2018-05-30 Impact factor: 15.419

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

1. The New Chemical Reporter 6-Alkynyl-6-deoxy-GlcNAc Reveals O-GlcNAc Modification of the Apoptotic Caspases That Can Block the Cleavage/Activation of Caspase-8.

2. Azide- and Alkyne-Bearing Metabolic Chemical Reporters of Glycosylation Show Structure-Dependent Feedback Inhibition of the Hexosamine Biosynthetic Pathway.

3. Metabolic Chemical Reporters of Glycans Exhibit Cell-Type-Selective Metabolism and Glycoprotein Labeling.

4. The Metabolic Chemical Reporter 6-Azido-6-deoxy-glucose Further Reveals the Substrate Promiscuity of O-GlcNAc Transferase and Catalyzes the Discovery of Intracellular Protein Modification by O-Glucose.

5. Changes in metabolic chemical reporter structure yield a selective probe of O-GlcNAc modification.

6. Substrate specificity provides insights into the sugar donor recognition mechanism of O-GlcNAc transferase (OGT).

7. Crystal structure of the capsular polysaccharide synthesizing protein CapE of Staphylococcus aureus.

8. Electrophilic probes for deciphering substrate recognition by O-GlcNAc transferase.

9. C-Terminal Tag Location Hampers in Vitro Profiling of OGT Peptide Substrates by mRNA Display.

10. Design and Synthesis of Metabolic Chemical Reporters for the Visualization and Identification of Glycoproteins.