(2R)-2-amino-3-[(triphenylmethyl)sulfanyl]propanoic acid

• ChemBase ID: 70101
• Molecular Formular: C22H21NO2S
• Molecular Mass: 363.47264
• Monoisotopic Mass: 363.12929992
• SMILES: C(=O)([C@@H](N)CSC(c1ccccc1)(c1ccccc1)c1ccccc1)O
• Canonical SMILES: N[C@H](C(=O)O)CSC(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C22H21NO2S/c23-20(21(24)25)16-26-22(17-10-4-1-5-11-17,18-12-6-2-7-13-18)19-14-8-3-9-15-19/h1-15,20H,16,23H2,(H,24,25)/t20-/m0/s1
• InChIKey: DLMYFMLKORXJPO-FQEVSTJZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-3-[(triphenylmethyl)sulfanyl]propanoic acid
• IUPAC Traditional name: (2R)-2-amino-3-[(triphenylmethyl)sulfanyl]propanoic acid
• Synonyms: S-Trityl-L-cysteine; (+)-S-Trityl-L-cysteine; H-Cys(Trt)-OH; (2R)-2-amino-3-[(triphenylmethyl)sulfanyl]propanoic acid; S-(Triphenylmethyl)-L-cysteine; (2R)-2-Amino-3-[(triphenylmethyl)thio]propanoic Acid; 3-Tritylthio-L-alanine; NSC 83265; S-Triphenylmethyl-L-cysteine; S-Trityl-(R)-cysteine; S-Tritylcysteine; Tritylthioalanine; S-Trityl-L-cysteine; S-三苯甲基-L-半胱氨酸; (+)-S-三苯甲基-L-半胱氨酸

Database IDs

• CAS Number: 2799-07-7
• MDL Number: MFCD00002611
• Beilstein Number: 2339626
• PubChem SID: 162035826; 24850097
• PubChem CID: 76044

CALCULATED PROPERTIES

• Acid pKa: 2.3713112
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.4407673
• LogD (pH = 7.4): 2.433321
• Log P: 2.440736
• Molar Refractivity: 108.0724 cm^3
• Polarizability: 42.008484 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: >160°C (dec.); 182-183 °C (dec.)(lit.); ca 185°C dec.
• Optical Rotation: [α]25/D +115°, c = 0.8 in 0.04 M ethanolic HCl; +84 (c=1 in acetic acid)
• Hydrophobicity(logP): 2.708

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C
• Storage Warning: IRRITANT
• RTECS: AY7710000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 22-24/25; 36
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• GHS Precautionary statements: P264-P270-P301+P312-P330-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 95+%; 97%
• Linear Formula: (C6H5)3CSCH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 02103137

Crystalline
Antileukemic activity in mice.

Sigma Aldrich - 164739

Application
Protected cysteine for peptide synthesis.
Packaging
5 g in glass bottle

Toronto Research Chemicals - T887350

A protected cysteine for peptide synthesis. S-Trityl-L-cysteine (STLC) is a tight-binding inhibitor of Eg5 that prevents mitotic progression. It has proven antitumor activity as shown in the NCI 60 tumor cell line screen.

REFERENCES

• Brier, S., et al.: Biochemistry, 43, 13072 (2004)
• Sakowicz, R., et al.: Cancer Res., 64, 3276 (2004)
• Zhu, C., et al.: Mol. Biol. Cell, 16, 3187 (2004)