(2S)-6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-2-aminohexanoic acid

• ChemBase ID: 126160
• Molecular Formular: C16H28N4O4S
• Molecular Mass: 372.48292
• Monoisotopic Mass: 372.1831264
• SMILES: O=C1N[C@@H]2[C@@H](SC[C@@H]2N1)CCCCC(=O)NCCCC[C@@H](C(=O)O)N
• Canonical SMILES: O=C(NCCCC[C@@H](C(=O)O)N)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C16H28N4O4S/c17-10(15(22)23)5-3-4-8-18-13(21)7-2-1-6-12-14-11(9-25-12)19-16(24)20-14/h10-12,14H,1-9,17H2,(H,18,21)(H,22,23)(H2,19,20,24)/t10-,11-,12-,14-/m0/s1
• InChIKey: BAQMYDQNMFBZNA-MNXVOIDGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-2-aminohexanoic acid
• IUPAC Traditional name: biocytin
• Synonyms: N6-[5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1-oxopentyl]-L-Lysine; Ne-Biotynyl-L-lysine; Bct; Nε-(+)-Biotinyl-L-lysine; Biocytin; Biotinyl-L-lysine; N_ε-(+)-Biotinyl-L-lysine; Biocytin

Database IDs

• CAS Number: 576-19-2
• MDL Number: MFCD00077319
• Beilstein Number: 97197
• PubChem SID: 162220501; 24891762
• PubChem CID: 7098660; 83814
• CHEBI ID: 27870
• Chemspider ID: 75634
• Wikipedia Title: Biocytin

CALCULATED PROPERTIES

• Acid pKa: 2.2447562
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -2.6114347
• LogD (pH = 7.4): -2.6142561
• Log P: -2.611381
• Molar Refractivity: 94.6605 cm^3
• Polarizability: 37.487923 Å^3
• Polar Surface Area: 133.55 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: ~245 °C; ~245 °C (dec.)(lit.); 253-255°C (dec.)
• Optical Rotation: [α]20/D +53°, c = 1.05% in 0.1 M NaOH(lit.)

Safety Information

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

Product Information

• Purity: ≥97.0% (HPLC); ≥98% (TLC)
• Empirical Formula (Hill Notation): C16H28N4O4S

DETAILS

Sigma Aldrich - B4261

包装
25, 50, 100, 250 mg in poly bottle
5 mg in glass bottle

Sigma Aldrich - 14409

Other Notes
A fluorometric assay for biotinidase (EC 3.5.1.12) using the natural substrate biocytin and 1,2-diacetylbenzene1; Preparation of biocytin-Sepharose® as affinity adsorbent for the single-step purification of avidin from egg white by affinity chromatography2
Legal Information
Sepharose is a registered trademark of GE Healthcare

Toronto Research Chemicals - B388100

Useful for the synthesis of Biocytin containing peptides to study the mechanism of reactions catalyzed by biotin - containing enzymes.

REFERENCES

• Bodanszky, M., and Fagan, D.T.: J. Am. Chem. Soc., 99, 235 (1977)