Metabolic label of GlcNAc/GalNAc residues
|Tags:||Azide, Bioorthogonal chemistry, Metabolic label, Mucin, N-Acetyl-Galactosamine, N-Acetyl-Glucosamine|
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P-GalNAz is an unnatural N-acetylgalactosamine derivative used for the metabolic labeling of GlcNAc/GalNAc residues in cells. P-GalNAz is passively taken-up by cells, converted to UDP-GalNAz and partially epimerized to UDP-GlcNAz by UDP-Glucose 4-epimerase (GALE). It was shown that the ratio of UDP-GlcNAz/UDP-GalNAz at equilibrium is 3/1.2 In addition, it was shown that P-GalNAz is more efficiently converted into UDP-GlcNAz than P-GlcNAz and hence a more efficient metabolic label of O-GlcNAc residues.2 The labeling efficiency and selectivity of P-GalNAz was shown to be dependent on the culture condition. Under high glucose conditions, P-GalNAz treatment resulted in Mucin O-glycan labeling. Under low glucose conditions, P-GalNAz labeled predominantly intracellular O-GlcNAc residues.3 P-GalNAz also leads to UDP-GalNAz which was shown to be preferentially incorporated into mucin O-glycans.1 Hence, the use of P-GalNAz leads to the labeling of O-GlcNAc and O-GalNAc residues mainly in intracelluar O-GlcNAc and extracellular mucin O-glycans, respectively. P-GalNAz contains an azide group for “click” chemistry using alkyne reagents. These alkynes can be modified with an affinity tag or fluorophore for example.
Metabolic labeling of GlcNAc/GalNAc residues in cells for isolation and visualization.
P-GalNAz is soluble in DMSO and PBS and is added to cell culture from a stock solution. Glycans decorated with GalNAz residues can be used to perform “click” chemistry. Please see our click chemistry page for suitable reaction partners.
CAS No.: 653600-56-7
Chemical formula: C16H22N4O10
Molecular weight: 430.37
Purity: > 95%
Identity: 1H NMR
Shipping temperature: 20°C
Storage temperature: 0°C
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