A click chemistry reagent
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Unmodified Version(s)
143252-deoxy-D-Glucose
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Product Categories

Product Type

Biochemicals
Labeling & Detection
Reactive Probes

Research Area

Cancer

Application

Click Chemistry

2-Azido-2-deoxy-D-glucose

Item No. 46553

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
56883-39-7
Synonyms
  • 2-Deoxy-2-azido-D-glucose
  • GlcAz
  • GlucN3
Molecular Formula
C6H11N3O5
Formula Weight
205.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly soluble: 0.1-1 mg/mlEthanol: Slightly soluble: 0.1-1 mg/mlPBS (pH 7.2): Sparingly soluble: 1-10 mg/ml
SMILES
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)N=[N+]=[N-]
InChi Code
InChI=1S/C6H11N3O5/c7-9-8-3(1-10)5(13)6(14)4(12)2-11/h1,3-6,11-14H,2H2/t3-,4+,5+,6+/m0/s1
InChi Key
MUIFUJRYFJTPGL-SLPGGIOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    2-Azido-2-deoxy-D-glucose is a click chemistry reagent and derivative of 2-deoxy-D-glucose (Item No. 14325).1,2 It has been used as a pretargeting agent in a murine Sarcoma 180 model, where it increases tumor uptake of the radiolabeled probe [99mTc(CO)3-C7] via an in vivo strain-promoted alkyne-azide cycloaddition (SPAAC) reaction.1 When conjugated to UDP, 2-azido-2-deoxy-D-glucose acts as a donor substrate for O-linked N-acetylglucosamine transferase (OGT) and can be incorporated into OGT substrates.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ding, J., Su, H., Wang, F., et al. A pre-targeting strategy for imaging glucose metabolism using technetium-99m labelled dibenzocyclooctyne derivative. Bioorg. Med. Chem. Lett. 29(14), 1791-1798 (2019).

    2. Shen, D.L., Liu, T.W., Zandberg, W., et al. Catalytic promiscuity of O-GlcNAc transferase enables unexpected metabolic engineering of cytoplasmic proteins with 2-azido-2-deoxy-glucose. ACS Chem. Biol. 12(1), 206-213 (2016).