(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-sulfanylpropanoic acid

• ChemBase ID: 157902
• Molecular Formular: C8H15NO4S
• Molecular Mass: 221.274
• Monoisotopic Mass: 221.07217897
• SMILES: CC(C)(C)OC(=O)N[C@@H](CS)C(=O)O
• Canonical SMILES: SC[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C8H15NO4S/c1-8(2,3)13-7(12)9-5(4-14)6(10)11/h5,14H,4H2,1-3H3,(H,9,12)(H,10,11)/t5-/m0/s1
• InChIKey: ATVFTGTXIUDKIZ-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-sulfanylpropanoic acid
• IUPAC Traditional name: (2R)-2-[(tert-butoxycarbonyl)amino]-3-sulfanylpropanoic acid
• Synonyms: Boc-L-cysteine; Boc-Cys-OH; Boc-L-半胱氨酸

Database IDs

• CAS Number: 20887-95-0
• MDL Number: MFCD00065565
• Beilstein Number: 2450705
• PubChem SID: 162252038; 24849407
• PubChem CID: 152319

CALCULATED PROPERTIES

• Acid pKa: 3.9227383
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.621859
• LogD (pH = 7.4): -2.2406516
• Log P: 0.961938
• Molar Refractivity: 53.0966 cm^3
• Polarizability: 21.053522 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D +8.0±1.5°, 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

• Purity: ≥98.5%
• Grade: for chiral derivatization
• Optical Purity: enantiomeric ratio: ≥99.5:0.5
• Empirical Formula (Hill Notation): C8H15NO4S

DETAILS

Sigma Aldrich - 15411

Other Notes
Chiral derivatizing agent used together with OPA for assaying the enantiomeric purity of amino acids1