608514-41-6
Chemical Structure
UDP-GlcNAz
- CAS No.: 608514-41-6
- Formula:C17H26N6O17P2
- Molecular Weight:648.37
InChIKey: JOCLDQLCBZCHFX-RTSQYROYSA-N
SMILES: O=C(C=CN1[C@H]2[C@H](O)[C@H](O)[C@@H](COP(OP(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3NC(CN=[N+]=[N-])=O)(O)=O)(O)=O)O2)NC1=O
Biological Activity: UDP-GlcNAz is a UDP sugar. UDP-GlcNAz transfers GlcNAz to serine and threonine residues during O-GlcNAcylation and causes GlcNAz modification of substrate proteins (including recombinant mouse iNOS), which can be detected via Staudinger ligation with biotin-phosphine. UDP-GlcNAz provides a click chemistry handle through its azide group for the enrichment and fluorescence detection of O-GlcNAcylated proteins[1][2][3][4].
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UDP-GlcNAz | UDP-GlcNAz is a UDP sugar. UDP-GlcNAz transfers GlcNAz to serine and threonine residues during O-GlcNAcylation and causes GlcNAz modification of substrate proteins (including recombinant mouse iNOS), which can be detected via Staudinger ligation with biotin-phosphine. UDP-GlcNAz provides a click chemistry handle through its azide group for the enrichment and fluorescence detection of O-GlcNAcylated proteins. | |||||||||||||||||||||
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References
- [1]. Abramowitz LK, et al. Chronically Elevated -GlcNAcylation Limits Nitric Oxide Production and Deregulates Specific Pro-Inflammatory Cytokines. Frontiers in immunology. 2022;13:802336.
- [2]. Jackson EG, et al. 4-Deoxy-4-fluoro-GalNAz (4FGalNAz) Is a Metabolic Chemical Reporter of O-GlcNAc Modifications, Highlighting the Notable Substrate Flexibility of O-GlcNAc Transferase. ACS chemical biology. 2022 Jan 21;17(1):159-170.
- [3]. Estevez A, et al. Molecular Interrogation to Crack the Case of O-GlcNAc. Chemistry (Weinheim an der Bergstrasse, Germany). 2020 Sep 21;26(53):12086-12100.
- [4]. Mayer A, et al. 6''-Azido-6''-deoxy-UDP-N-acetylglucosamine as a glycosyltransferase substrate. Bioorganic & medicinal chemistry letters. 2011 Feb 15;21(4):1199-201.
