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

• ChemBase ID: 90918
• Molecular Formular: C21H36N4O6S
• Molecular Mass: 472.59874
• Monoisotopic Mass: 472.23555589
• SMILES: O=C1N[C@@H]2[C@@H](SC[C@@H]2N1)CCCCC(=O)NCCCC[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• Canonical SMILES: O=C(CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2)NCCCC[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C21H36N4O6S/c1-21(2,3)31-20(30)24-13(18(27)28)8-6-7-11-22-16(26)10-5-4-9-15-17-14(12-32-15)23-19(29)25-17/h13-15,17H,4-12H2,1-3H3,(H,22,26)(H,24,30)(H,27,28)(H2,23,25,29)/t13-,14-,15-,17-/m0/s1
• InChIKey: XTQNFOCBPUXJCS-JKQORVJESA-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-{[(tert-butoxy)carbonyl]amino}hexanoic acid
• IUPAC Traditional name: (2S)-6-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}-2-[(tert-butoxycarbonyl)amino]hexanoic acid
• Synonyms: N-t-BOC-biocytin; Nα-Boc-Nε-biotinyl-L-lysine; Nε-Biotinyl-Nα-Boc-L-lysine; Nα-Boc-biocytin; N2-[(1,1-Dimethylethoxy)carbonyl]-N6-[5-[(3aS,4S,6aR)-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1-oxopentyl]-L-lysine; Nα-Boc-Nε-生物素基-L-赖氨酸; Nε-生物素基-Nα-Boc-L-赖氨酸; Nα-Boc-生物胞素

Database IDs

• CAS Number: 62062-43-5
• MDL Number: MFCD00133628
• Beilstein Number: 5797526
• PubChem SID: 162077622; 24849068
• PubChem CID: 16211301

CALCULATED PROPERTIES

• Acid pKa: 3.9344199
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -0.42948574
• LogD (pH = 7.4): -2.0523949
• Log P: 1.1431013
• Molar Refractivity: 119.5335 cm^3
• Polarizability: 47.12176 Å^3
• Polar Surface Area: 145.86 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: >132°C dec.; 132°C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C21H36N4O6S

DETAILS

Apollo Scientific Ltd - OR6301T

An intermediate for the synthesis of biocytin-containingpeptides.

Sigma Aldrich - 15083

Packaging
500 mg in poly tube

Toronto Research Chemicals - B630000

An intermediate in the synthesis of biocytin-containing peptides.

REFERENCES

• Bodansky, M., and Fagen, D.T.: J. Am. Chem. Soc., 99, 235 (1977)
• Hodges, J., et al.: Bioorg. Med. Chem. Lett., 3, 905 (1977)