2,5-dioxopyrrolidin-1-yl 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoate

• ChemBase ID: 133765
• Molecular Formular: C14H19N3O5S
• Molecular Mass: 341.38276
• Monoisotopic Mass: 341.10454172
• SMILES: C1CC(=O)N(C1=O)OC(=O)CCCC[C@H]1[C@@H]2[C@H](CS1)NC(=O)N2
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C14H19N3O5S/c18-10-5-6-11(19)17(10)22-12(20)4-2-1-3-9-13-8(7-23-9)15-14(21)16-13/h8-9,13H,1-7H2,(H2,15,16,21)/t8-,9-,13-/m0/s1
• InChIKey: YMXHPSHLTSZXKH-RVBZMBCESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanoate
• Synonyms: Biotin-NHS; N-Hydroxysuccimidobiotin; (+)-Biotin N-succinimidyl ester; d-Biotin NHS ester; BNHS; Biotinyl-N-hydroxy-succinimide; N-Hydroxysuccinimidobiotin; N-Succinimidyl D-biotinate; NHS-Biotin; (+)-Biotin N-hydroxysuccinimide ester; Biotin-OSu; (+)-生物素-N-羟基琥珀酰亚胺酯

Database IDs

• CAS Number: 35013-72-0
• MDL Number: MFCD00078531
• Beilstein Number: 4720781
• PubChem SID: 162228042; 24895479
• PubChem CID: 6710714

CALCULATED PROPERTIES

• Acid pKa: 13.314536
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.310991
• LogD (pH = 7.4): -0.31099144
• Log P: -0.31099096
• Molar Refractivity: 80.6047 cm^3
• Polarizability: 31.979704 Å^3
• Polar Surface Area: 104.81 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: ≤50 mg/mL (Stable for at least one month in dry DMF); DMSO: soluble
• Apperance: powder; Powder
• Melting Point: 212-214 °C
• Optical Rotation: [α]20/D +53±1°, c = 1% in DMF

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥95% (HPLC); ≥98% (HPLC); 98%
• Quality Level: GMP
• Empirical Formula (Hill Notation): C14H19N3O5S

DETAILS

Sigma Aldrich - H1759

Application
May be used in the biotinylation of proteins and peptides. Typically coupled to primary amine in the pH range 6.5-8.5.

Sigma Aldrich - 14405

Other Notes
Activated biotin, generally used for attaching biotin to amino acids, peptides and proteins1; Review: The use of the avidin-biotin complex as a tool in molecular biology2; On-resin biotinylation of chemically synthesized proteins for one-step purification3