Biotin with a terminal azide group
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Product Categories

Product Type

Biochemicals
Labeling & Detection
Reactive Probes

Research Area

Lipid Biochemistry

Application

Click Chemistry

Biotin-azide

Item No. 13040

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3aS,4S,6aR)-N-(3-azidopropyl)hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanamide
CAS Number
908007-17-0
Synonyms
  • Azido-biotin
  • Click Tag™ Biotin-azide
Molecular Formula
C13H22N6O2S
Formula Weight
326.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 5 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlPBS (pH 7.2): Sparingly (< 100 µg/ml)
SMILES
O=C(N1)N[C@]([C@]1([H])CS2)([H])[C@@H]2CCCCC(NCCCN=[N+]=[N-])=O
InChi Code
InChI=1S/C13H22N6O2S/c14-19-16-7-3-6-15-11(20)5-2-1-4-10-12-9(8-22-10)17-13(21)18-12/h9-10,12H,1-8H2,(H,15,20)(H2,17,18,21)/t9-,10-,12-/m0/s1
InChi Key
SWODDJWJUGOAQB-NHCYSSNCSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Biotin-azide is a form of biotin with a terminal azide group. It is used to add biotin to other molecules that bear either an alkyne group, through click chemistry, or a phosphine group, using Staudinger ligation.1,2 Biotin-azide has been commonly used to biotin-tag alkynylated lipids, particularly those associated with proteins through post-translational modification.1,3,4 It can also be used to biotin-tag proteins, lipids, carbohydrates, and nucleic acids that have been modified with alkyne or phosphine groups.5,6,7,8

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Yap, M.C., Kostiuk, M.A., Martin, D.D.O., et al. Rapid and selective detection of fatty acylated proteins using ω-alkynyl-fatty acids and click chemistry. J. Lipid Res. 51(6), 1566-1580 (2010).

    2. Zhang, J., Li, S., Zhang, D., et al. Reductive ligation mediated one-step disulfide formation of S-nitrosothiols. Org. Lett. 12(18), 4208-4211 (2010).

    3. Kim, H.Y.H., Tallman, K.A., Liebler, D.C., et al. An azido-biotin reagent for use in the isolation of protein adducts of lipid-derived electrophiles by streptavidin catch and photorelease. Mol. Cell. Proteomics 8(9), 2080-2089 (2009).

    4. Yount, J.S., Zhang, M.M., and Hang, H.C. Visualization and identification of fatty acylated proteins using chemical reporters. Curr. Protoc. Chem. Biol. 3(2), 65-79 (2011).

    5. Ma, Y., Zhang, H., Gruzdys, V., et al. Azide-reactive liposome for chemoselective and biocompatible liposomal surface functionalization and glyco-liposomal microarray fabrication. Langmuir 27(21), 13097-13103 (2011).

    6. Crump, C.J., am Ende, C.W., Ballard, T.E., et al. Development of clickable active site-directed photoaffinity probes for γ-secretase. Bioorg. Med. Chem. Lett. 22(8), 2997-3000 (2012).

    7. Sohn, C.H., Agnew, H.D., Lee, J.E., et al. Designer reagents for mass spectrometry-based proteomics: Clickable cross-linkers for elucidation of protein structures and interactions. Anal. Chem. 84(6), 2662-2669 (2012).

    8. Al-Shareffi, E., Chaubard, J.L., Leonhard-Melief, C., et al. 6-alkynyl fucose is a bioorthogonal analog for O-fucosylation of epidermal growth factor-like repeats and thrombospondin type-1 repeats by protein O-fucosyltransferases 1 and 2. Glycobiology 23(2), 188-198 (2013).