P-GlcNAlk

Selective metabolic label of GlcNAc residues

Product ID: SV3915
Synonyms: Ac4GlcNPent; Ac4GlcNAlk
Tags: Alkyne, Bioorthogonal chemistry, Metabolic label, N-Acetyl-Glucosamine
P-GlcNAlk
Product Price Estimated Shipping Time Purchase
P-GlcNAlk - 10 mg
200.00 1-3 days
P-GlcNAlk - 25 mg
400.00 1-3 days
P-GlcNAlk - 100 mg
950.00 1-3 days

Product information

  • Function

    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.

  • Applications

    Metabolic labeling of GlcNAc residues in cells for isolation and visualization.

  • Handling

    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.

  • Chemical Information

    CAS No.: NA
    SMILES: O=C(CCC#C)N[C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)OC1OC(C)=O
    Chemical formula: C19H25NO10
    Molecular weight: 427.40
    Purity: > 95%
    Identity: 1H NMR
    Shipping temperature: 20°C
    Storage temperature: 0°C

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