bis(4-methylbenzene-1-sulfonic acid) prop-2-en-1-yl (2R)-2-amino-3-{[(2R)-2-amino-3-oxo-3-(prop-2-en-1-yloxy)propyl]disulfanyl}propanoate

• ChemBase ID: 156768
• Molecular Formular: C26H36N2O10S4
• Molecular Mass: 664.83144
• Monoisotopic Mass: 664.12527936
• SMILES: Cc1ccc(cc1)S(=O)(=O)O.Cc1ccc(cc1)S(=O)(=O)O.C=CCOC(=O)[C@H](CSSC[C@@H](C(=O)OCC=C)N)N
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)O.Cc1ccc(cc1)S(=O)(=O)O.C=CCOC(=O)[C@H](CSSC[C@@H](C(=O)OCC=C)N)N
• InChI: InChI=1S/C12H20N2O4S2.2C7H8O3S/c1-3-5-17-11(15)9(13)7-19-20-8-10(14)12(16)18-6-4-2;2*1-6-2-4-7(5-3-6)11(8,9)10/h3-4,9-10H,1-2,5-8,13-14H2;2*2-5H,1H3,(H,8,9,10)/t9-,10-;;/m0../s1
• InChIKey: QLKBMTUQCIEQNW-BZDVOYDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(4-methylbenzene-1-sulfonic acid) prop-2-en-1-yl (2R)-2-amino-3-{[(2R)-2-amino-3-oxo-3-(prop-2-en-1-yloxy)propyl]disulfanyl}propanoate
• IUPAC Traditional name: bis(toluenesulfonic acid) prop-2-en-1-yl (2R)-2-amino-3-{[(2R)-2-amino-3-oxo-3-(prop-2-en-1-yloxy)propyl]disulfanyl}propanoate
• Synonyms: L-Cystine bisallyl ester di(p-toluenesulfonate) salt; L-胱氨酸双烯丙酯 二(对甲苯磺酸) 盐

Database IDs

• CAS Number: 142601-71-6
• MDL Number: MFCD00043424
• Beilstein Number: 7966375
• PubChem SID: 24858244; 162250905
• PubChem CID: 16211921

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.509299
• LogD (pH = 7.4): 0.12227272
• Log P: 0.3814036
• Molar Refractivity: 82.7354 cm^3
• Polarizability: 33.12833 Å^3
• Polar Surface Area: 104.64 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 175-180 °C
• Optical Rotation: [α]20/D -11.5±1°, c = 3% in methanol

Safety Information

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

Product Information

• Purity: ≥95.0% (sum of enantiomers, TLC)
• Linear Formula: CH2=CHCH2OCOCH(NH2)CH2SSCH2CH(NH2)COOCH2CH=CH2.2C7H8O3S

DETAILS

Sigma Aldrich - 30230

Other Notes
Used in peptide and N-glycopeptide synthesis; the ester is selectively deblocked with (Ph3P)3RhCl1
Packaging
10 g in glass bottle