N'-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoyl}-6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanehydrazide

• ChemBase ID: 155491
• Molecular Formular: C20H29N5O5S
• Molecular Mass: 451.53976
• Monoisotopic Mass: 451.18894005
• SMILES: C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)NNC(=O)CCCCCN1C(=O)C=CC1=O)NC(=O)N2
• Canonical SMILES: O=C(NNC(=O)CCCCCN1C(=O)C=CC1=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C20H29N5O5S/c26-15(7-2-1-5-11-25-17(28)9-10-18(25)29)23-24-16(27)8-4-3-6-14-19-13(12-31-14)21-20(30)22-19/h9-10,13-14,19H,1-8,11-12H2,(H,23,26)(H,24,27)(H2,21,22,30)/t13-,14-,19-/m0/s1
• InChIKey: VAPZWEFPQRDVHR-NJSLBKSFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N'-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoyl}-6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanehydrazide
• IUPAC Traditional name: N'-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanoyl}-6-(2,5-dioxopyrrol-1-yl)hexanehydrazide
• Synonyms: N-Biotinoyl-N′-(6-maleimidohexanoyl)hydrazide; Biotin-maleimide

Database IDs

• PubChem SID: 162249629
• PubChem CID: 195196

CALCULATED PROPERTIES

• Acid pKa: 10.3811865
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -0.37306
• LogD (pH = 7.4): -0.37345648
• Log P: -0.3730549
• Molar Refractivity: 115.0844 cm^3
• Polarizability: 44.38855 Å^3
• Polar Surface Area: 136.71 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetic acid: soluble20 mg/mL
• Apperance: powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (TLC)
• Empirical Formula (Hill Notation): C20H29N5O5S

DETAILS

Sigma Aldrich - B1267

Application
Biotin-maleimide- 0.01 mg/ml in PBS containing 0.1% Tween 20, incubated for 1 h at room temperature can be used to detect deprotected cysteine thiols present on immobilized peptides1.
Sulfhydryl-specific biotinylation reagent. Couples by highly efficient thioether linkage. Typically used to couple to intrinsic sulfhydryls, e.g. protein, and avoid modification of primary amine.
General description
Biotin-maleimide is a biotin specific thiol containing reagent used to biotinylate different proteins through artificially induced or natural sulphadryl group. It can be used as a universal, multipurpose, thiol-specific probe. Biotin-maleimide can also be used in dot blots to detect protein SH groups2.