(2R)-2-amino-3-(tert-butyldisulfanyl)propanoic acid

• ChemBase ID: 132390
• Molecular Formular: C7H15NO2S2
• Molecular Mass: 209.3295
• Monoisotopic Mass: 209.05442073
• SMILES: CC(C)(C)SSC[C@@H](C(=O)O)N
• Canonical SMILES: N[C@H](C(=O)O)CSSC(C)(C)C
• InChI: InChI=1S/C7H15NO2S2/c1-7(2,3)12-11-4-5(8)6(9)10/h5H,4,8H2,1-3H3,(H,9,10)/t5-/m0/s1
• InChIKey: TWMBHZTWEDJDRC-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-(tert-butyldisulfanyl)propanoic acid
• IUPAC Traditional name: (2R)-2-amino-3-(tert-butyldisulfanyl)propanoic acid
• Synonyms: 3-(tert-Butyldithio)-L-alanine; S-(tert-Butylthio)-L-cysteine; S-tert-Butylmercapto-L-cysteine; S-(tert-Butylthio)-L-cysteine hydrate; S-(叔丁基硫代)-L-半胱氨酸 水合物

Database IDs

• CAS Number: 313223-16-4; 30044-51-0
• EC Number: 250-012-7
• MDL Number: MFCD00002609
• Beilstein Number: 2247500
• PubChem SID: 24891874; 162226667
• PubChem CID: 7006457

CALCULATED PROPERTIES

• Acid pKa: 2.4111493
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.2961979
• LogD (pH = 7.4): -1.3051118
• Log P: -1.2962536
• Molar Refractivity: 54.7317 cm^3
• Polarizability: 21.846231 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~190 °C (dec.); 177 °C (dec.)(lit.)
• Optical Rotation: [α]20/D -83±3°, c = 1% in 1 M HCl; [α]21/D -82°, c = 2 in 1 M HCl

Safety Information

• German water hazard class: 3
• Safety Statements: 22-24/25

Product Information

• Purity: ≥95.0% (T); 98%
• Grade: purum
• Ignition Residue: ≤0.05%
• Impurities: ≤0.5% free cysteine
• Linear Formula: (CH3)3CSSCH2CH(NH2)CO2H·xH2O
• Empirical Formula (Hill Notation): C7H15NO2S2

DETAILS

Sigma Aldrich - 232351

Packaging
5 g in glass bottle

Sigma Aldrich - 20235

Other Notes
Important S-protected cysteine-derivative for peptide synthesis1