Metabolic label of GlcNAc/GalNAc residues
|Tags:||Alkyne, Bioorthogonal chemistry, Metabolic label, N-Acetyl-Glucosamine|
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P-GalNPoc is an unnatural N-Acetylgalactosamine derivative used for the metabolic labeling of GlcNAc/GalNAc residues in cells.1
Mode of action
P-GalNPoc is passively taken-up by cells and converted into UDP-GalPoc and epimerized to UDP-GlcNPoc by GALE inside cells and incorporated in glycans. Labeling with P-GalNPoc showed labeling of a known intracellular O-GlcNAcylated protein NEDD4 hence confirming incorporation as a GlcNAc surrogate. Labeling with P-GalNPoc was shown to be less efficient for NEDD4 labeling compared to other HexNAc derivatives such as P-ManNPoc and P-GlcNPoc.1 Cell surface labeling of P-GalNPoc was also much weaker compared to P-ManNPoc and P-GlcNPoc, consistent with the lower labeling observed for P-GalNAlk.1 However, in contrast to P-GalNAlk, P-GalNPoc is a substrate for GALE and epimerized to UDP-GlcNPoc. P-GalNPoc contains a Poc group for “click” chemistry with azide reagents. These azides can be modified with an affinity tag or fluorophore for example.
Metabolic labeling of GlcNAc/GalNAc residues in cells for isolation and visualization.
P-GalNPoc is soluble in DMSO and PBS and is added to cell culture from a stock solution. Incubation of the cells with P-GalNPoc results in a detectable signal after 4 hrs. Glycans decorated with GlcNPoc residues can be used to perform “click” chemistry. Please see our click chemistry page for suitable reaction partners.
CAS No.: 1431120-34-1
Chemical formula: C18H23NO11
Molecular weight: 429.37
Purity: > 95%
Identity: 1H NMR
Shipping temperature: 20°C
Storage temperature: 0°C
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