| Identification | Back Directory | [Name]
BIOTIN HPDP | [CAS]
129179-83-5 | [Synonyms]
Biotin Impurity 31
Pyridyldithiol-biotin
Biotin HPDP,BiotinHPDP
Pyridyldisulfide-biotin
Macamide Impurity 11(Biotin HPDP)
N-[6-(Biotinamido)hexyl]-3'-(2'-pyridyldithio)propionamide
N-[6-(BiotinaMido)hexyl]-3`-(2`-pyridyldithio)propionaMide(Biotin-HPDP)
(3aS,4S,6aR)-Hexahydro-2-oxo-N-[6-[[1-oxo-3-(2-pyridinyldithio)propyl]amino]hexyl]-1H-thieno[3,4-d]imidazole-4-pentanamide
5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-N-(6-(3-(pyridin-2-yldisulfanyl)propanamido)hexyl)pentanamide
1H-Thieno[3,4-d]imidazole-4-pentanamide, hexahydro-2-oxo-N-[6-[[1-oxo-3-(2-pyridinyldithio)propyl]amino]hexyl]-, (3aS,4S,6aR)- | [Molecular Formula]
C24H37N5O3S3 | [MDL Number]
MFCD00078541 | [MOL File]
129179-83-5.mol | [Molecular Weight]
539.78 |
| Chemical Properties | Back Directory | [Melting point ]
160-163°C | [Boiling point ]
876.0±65.0 °C(Predicted) | [density ]
1.28 | [storage temp. ]
-20°C Freezer | [solubility ]
insoluble in H2O; ≥101.4 mg/mL in DMSO; ≥8.29 mg/mL in EtOH with ultrasonic | [form ]
powder to crystal | [pka]
13.90±0.40(Predicted) | [color ]
White to Light yellow | [InChIKey]
QLPHBNRMJLFRGO-YDHSSHFGSA-N | [SMILES]
C1(=O)N[C@]2([H])[C@H](CCCCC(NCCCCCCNC(=O)CCSSC3=NC=CC=C3)=O)SC[C@]2([H])N1 |
| Hazard Information | Back Directory | [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. Biotin-HPDP is also used in the biotin switch technique to tag S-nitrosylated (SNO) proteins, following reduction of SNO groups to thiols. 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. | [Chemical Properties]
Pale Yellow Solid | [Uses]
This compounds reacts specifically with thiol groups. | [Application]
Mustafa et al. applied S-methylmethanethiosulfonate (MMTS) and N-(6-(biotinamido)hexyl)-3′-(2′-pyridyldithio)propionamide (BIOTIN HPDP) to detect protein polysulfidation. The assumption was that MMTS exclusively blocks −SH, while BIOTIN HPDP can tag −SSH[6]. | [References]
[1] CHANGYUAN LU. S-sulfhydration/desulfhydration and S-nitrosylation/denitrosylation: A common paradigm for gasotransmitter signaling by H2S and NO[J]. Methods, 2013, 62 2: Pages 177-181. DOI: 10.1016/j.ymeth.2013.05.020
[2] S. SLATIN. Translocation of a functional protein by a voltage-dependent ion channel[J]. Proceedings of the National Academy of Sciences of the United States of America, 2002, 99 1: 1286-1291. DOI: 10.1073/pnas.022480199
[3] OSCAR A. BIZZOZERO Jianzheng Z. Identification of major S-nitrosylated proteins in murine experimental autoimmune encephalomyelitis[J]. Journal of Neuroscience Research, 2009, 87 13: 2881-2889. DOI: 10.1002/jnr.22113
[4] KARINA CKLESS . In situ detection and visualization of S-nitrosylated proteins following chemical derivatization: identification of Ran GTPase as a target for S-nitrosylation[J]. Nitric oxide?: biology and chemistry, 2004, 11 3: Pages 216-227. DOI: 10.1016/j.niox.2004.06.002
[5] MICHAEL T FORRESTER Jonathan S S Matthew W Foster. Assessment and application of the biotin switch technique for examining protein S-nitrosylation under conditions of pharmacologically induced oxidative stress.[J]. The Journal of Biological Chemistry, 2007, 282 19: 13977-13983. DOI: 10.1074/jbc.m609684200 |
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