S-Trityl-D-cysteine
S-Trityl-D-cysteine Basic information
- Product Name:
- S-Trityl-D-cysteine
- Synonyms:
-
- S-(Triphenylmethyl)-D-cysteine
- 2-amino-3-[tri(phenyl)methylsulfanyl]propanoic acid
- 2-amino-3-[tri(phenyl)methylthio]propionic acid
- 2-azanyl-3-[tri(phenyl)methylsulfanyl]propanoic acid
- (S)-2-AMino-3-(tritylthio)propanoic acid
- D-Cys(Trt)-OH
- S-Trityl-D-cysteine99%
- (2S)-2-amino-3-[(triphenylmethyl)sulfanyl]propanoic acid
- CAS:
- 25840-82-8
- MF:
- C22H21NO2S
- MW:
- 363.47
- Mol File:
- 25840-82-8.mol
S-Trityl-D-cysteine Chemical Properties
- Boiling point:
- 524.7±50.0 °C(Predicted)
- Density
- 1.232±0.06 g/cm3(Predicted)
- storage temp.
- under inert gas (nitrogen or Argon) at 2–8 °C
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- pka
- 2.22±0.10(Predicted)
- form
- Solid
- color
- White to off-white
- optical activity
- Consistent with structure
- Water Solubility
- Sparingly soluble in water 0.022 g/L 25°C.
S-Trityl-D-cysteine Usage And Synthesis
Uses
(-)-S-Trityl-D-cysteine is used in medicine as intermediate. It inhibits the human mitotic kinesin Eg5.
Synthesis
76-84-6
921-01-7
2799-07-7
General procedure for the synthesis of S-triphenylmethyl-L-cysteine from triphenylmethanol and D-cysteine: D-cysteine (242.30 mg, 2.0 mmol) was placed in a single-necked flask, trifluoroacetic acid (TFA, 4 mL) was added and stirred at room temperature. Triphenylmethanol (520.68 mg, 2.0 mmol) was then added and the reaction continued to be stirred at room temperature for 2 hours. After completion of the reaction, the reaction mixture was cooled to 0 °C, anhydrous ether (30 mL) was added, and the pH was adjusted to 4-5 by slowly adding 4 N NaOH aqueous solution dropwise with stirring.Next, 10% saturated sodium acetate aqueous solution was added, and stirring was continued for 1 h to stabilize the pH at 5-6.The reaction mixture was filtered, and the filter cake was washed with anhydrous ether (30 mL × 2) to afford the white powdery product S Triphenylmethyl-L-cysteine (566.4 mg, yield: 77.90%).
References
[1] Patent: CN106432014, 2017, A. Location in patent: Paragraph 0199; 0200; 0201; 0202
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