(2R)-3-{[(2R)-2-carboxy-2-(phenylformamido)ethyl]disulfanyl}-2-(phenylformamido)propanoic acid

• ChemBase ID: 152287
• Molecular Formular: C20H20N2O6S2
• Molecular Mass: 448.5126
• Monoisotopic Mass: 448.07627837
• SMILES: c1ccc(cc1)C(=O)N[C@@H](CSSC[C@@H](C(=O)O)NC(=O)c1ccccc1)C(=O)O
• Canonical SMILES: OC(=O)[C@@H](NC(=O)c1ccccc1)CSSC[C@@H](C(=O)O)NC(=O)c1ccccc1
• InChI: InChI=1S/C20H20N2O6S2/c23-17(13-7-3-1-4-8-13)21-15(19(25)26)11-29-30-12-16(20(27)28)22-18(24)14-9-5-2-6-10-14/h1-10,15-16H,11-12H2,(H,21,23)(H,22,24)(H,25,26)(H,27,28)/t15-,16-/m0/s1
• InChIKey: GUTXMPQWQSOAIY-HOTGVXAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-{[(2R)-2-carboxy-2-(phenylformamido)ethyl]disulfanyl}-2-(phenylformamido)propanoic acid
• IUPAC Traditional name: (2R)-3-{[(2R)-2-carboxy-2-(phenylformamido)ethyl]disulfanyl}-2-(phenylformamido)propanoic acid
• Synonyms: N,N′-Dibenzoyl-L-cystine; N,N′-二苯甲酰基-L-胱氨酸

Database IDs

• CAS Number: 25129-20-8
• EC Number: 246-640-6
• MDL Number: MFCD00063220
• Beilstein Number: 2068210
• PubChem SID: 24860333; 162246432
• PubChem CID: 13479156

CALCULATED PROPERTIES

• Acid pKa: 2.989745
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.3499713
• LogD (pH = 7.4): -4.8591323
• Log P: 1.9731579
• Molar Refractivity: 115.1004 cm^3
• Polarizability: 43.92961 Å^3
• Polar Surface Area: 132.8 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 195-200 °C (dec.)
• Optical Rotation: [α]20/D -215±8°, c = 1% in ethanol

Safety Information

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

Product Information

• Empirical Formula (Hill Notation): C20H20N2O6S2

DETAILS

Sigma Aldrich - 33562

Other Notes
Chiral modifier of LiBH4 for enantioselective reductions of aromatic, heteroaromatic and unsaturated ketones to alcohols6,7,8,9
Packaging
5 g in glass bottle
Application
Reactant involved in:
• Synthesis of integrin antagonists1
• Dissipative self-assembly of molecular gelator using chemical fuel2
• Synthesis of crosslinkable hydrogel for proliferation of encapsulated human derm fibroblast3
• Analysis for use as metallo-β-lactamase inhibitors4
• Amplification of bifunctional disulfide ligands for calmodulin5