A sulfhydryl-reactive biotinylation reagent
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Biotin-HPDP

Item No. 16459

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3aS,4S,6aR)-hexahydro-2-oxo-N-[6-[[1-oxo-3-(2-pyridinyldithio)propyl]amino]hexyl]-1H-thieno[3,4-d]imidazole-4-pentanamide
CAS Number
129179-83-5
Molecular Formula
C24H37N5O3S3
Formula Weight
539.8
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/ml
λmax
237, 284 nm
SMILES
O=C1N[C@@]2([H])[C@@](CS[C@H]2CCCCC(NCCCCCCNC(CCSSC3=CC=CC=N3)=O)=O)([H])N1
InChi Code
InChI=1S/C24H37N5O3S3/c30-20(10-4-3-9-19-23-18(17-33-19)28-24(32)29-23)25-13-6-1-2-7-14-26-21(31)12-16-34-35-22-11-5-8-15-27-22/h5,8,11,15,18-19,23H,1-4,6-7,9-10,12-14,16-17H2,(H,25,30)(H,26,31)(H2,28,29,32)/t18-,19-,23-/m0/s1
InChi Key
QLPHBNRMJLFRGO-YDHSSHFGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

    $36

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    10 mg

    $68

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    50 mg

    $253

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    Product Description

    Biotin-HPDP is a sulfhydryl-reactive biotinylation reagent that forms a reversible disulfide linkage. It is used to label protein cysteines and other substrates that contain sulfhydryl groups.1,2,3 Biotin-HPDP is also used in the biotin switch technique to tag S-nitrosylated (SNO) proteins, following reduction of SNO groups to thiols.4,5 Compounds that are tagged with biotin interact avidly with streptavidin-coupled beads, fluorophores, enzymes, etc. The interaction of biotin-HPDP with substrates containing sulfhydryl groups is easily performed at pH 6.5 to 7.5 in buffers such as PBS. The disulfide linkage that is formed between avidin and substrate can later by cleaved by a reducing agent, like dithiothreitol.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lu, C., Kavalier, A., Lukyanov, E., et al. S-sulfhydration/desulfhydration and S-nitrosylation/denitrosylation: A common paradigm for gasotransmitter signaling by H2S and NO. Methods 62(2), 177-181 (2013).

    2. Slatin, S.L., Nardi, A., Jakes, K.S., et al. Translocation of a functional protein by a voltage-dependent ion channel. Proc. Natl. Acad. Sci. USA 99(3), 1286-1291 (2002).

    3. Bizzozero, O.A., and Zheng, J. Identification of major S-nitrosylated proteins in murine experimental autoimmune encephalomyelitis. J. Neurosci. Res. 87(13), 2881-2889 (2009).

    4. Ckless, K., Reynaert, N.L., Taatjes, D.J., et al. In situ detection and visualization of S-nitrosylated proteins following chemical derivatization: Identification of Ran GTPase as a target for S-nitrosylation. Nitric Oxide 11, 216-227 (2004).

    5. Forrester, M.T., Foster, M.W., and Stamler, J.S. Assessment and application of the biotin switch technique for examining protein S-Nitrosylation under conditions of pharmacologically induced oxidative stress. The Journal of Biological Chemisty 282(19), 13977-13983 (2007).