Selective metabolic label of GlcNAc residues
|Tags:||Alkyne, Bioorthogonal chemistry, Metabolic label, N-Acetyl-Glucosamine|
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Selective metabolic labeling of GlcNAc containing glycans in cells.
Mode of action
P-GlcNAlk is an unnatural N-acetylglucosamine derivative used for the metabolic labeling of GlcNAc residues in cells.1 P-GlcNAlk is passively taken-up by cells, converted to UDP-GlcNAlk and incorporated in glycans. Labeling with P-GlcNAlk demonstrated that depending on the conditions, N-glycans and intracellular O-GlcNAc residues were labeled. Under high glucose conditions, P-GlcNAlk treatment resulted in N-glycans labeling (labeling signal was sensitive for PNGase-F treatment). Under low glucose conditions, P-GlcNAlk labeled mostly intracellular O-GlcNAc residues.1 Furthermore, it was shown that UDP-GlcNAlk is not epimerized to UDP-GalNAlk and vica versa and hence represents a very specific label of GlcNAc residues. Compared to other probes that can be used to label GlcNAc residues (P-GlcNPoc, P-GlcNAz, P-GalNAz) P-GlcNAlk is a more specific probe as it is not readily interconverted to other monosaccharides. Due to its specificity, P-GlcNAlk was used to identify new glycoproteins using metabolic labeling. The glycosylation of NEDD4-1 was discovered using P-GlcNAlk. P-GlcNAlk contains an alkyne group for “click” chemistry using azide reagents. These azides can be modified with an affinity tag or fluorophore for example.
Metabolic labeling of GlcNAc residues in cells for isolation and visualization.
P-GlcNAlk is soluble in DMSO and PBS and is added to cell culture from a stock solution. Glycans decorated with GlcNAlk residues can be used to perform “click” chemistry. Please see our click chemistry page for suitable reaction partners.
CAS No.: NA
Chemical formula: C19H25NO10
Molecular weight: 427.40
Purity: > 95%
Identity: 1H NMR
Shipping temperature: 20°C
Storage temperature: 0°C
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