S-Trityl-L-cysteine Chemical Properties

Melting point:

182-183 °C (dec.)(lit.)

Boiling point:

524.7±50.0 °C(Predicted)

Density 

1.1342 (rough estimate)

refractive index 

111 ° (C=0.8, 0.04mol Ethanolic HCl)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in DMSO (up to 20 mg/ml).

form 

White to off-white solid.

pka

2.22±0.10(Predicted)

color 

White or off-white

optical activity

[α]25/D +115°, c = 0.8 in 0.04 M ethanolic HCl

BRN 

2339626

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 week.

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

SMILES

C(O)(=O)[C@H](CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)N

CAS DataBase Reference

2799-07-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

AY7710000

HS Code 

29309090

Toxicity

dog,LDLo,intravenous,150mg/kg (150mg/kg),GASTROINTESTINAL: NAUSEA OR VOMITINGGASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),National Technical Information Service. Vol. PB81-109993,

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

S-Trityl-L-cysteine Usage And Synthesis

Description

S-Trityl-cysteine (2799-07-7) is a cell permeable inhibitor of mitotic kinesin Eg5 (IC50 for inhibition of basal ATPase activity = 1 μM; IC50 for inhibition of microtubule-activated ATPase activity = 140 nM). Mean growth concentration (GI50) of 1.31 μM for a panel of 60 different tumor cell lines.

Chemical Properties

almost white to light yellow granular powder

Uses

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.

Uses

(+)-S-Trityl-L-cysteine, a non-natural, sulfur-containing amino acid is commonly used as a reagent in solution phase peptide synthesis (SPPS). It is also used as a metal-binding agent to synthesize substituted ferrocenoyl peptide conjugates using HBTU peptide coupling reagent for the cation-sensing applications solution via peptide-metal interactions.

Definition

ChEBI: (2R)-2-amino-3-[(triphenylmethyl)thio]propanoic acid is a benzenoid aromatic compound.

reaction suitability

reaction type: solution phase peptide synthesis

Biological Activity

Potent, cell-permeable, selective inhibitor of mitotic kinesin Eg5, a protein required for establishing and maintaining a bipolar spindle. Inhibits basal ATPase activity (IC 50 = 1 mM) and microtubule-activated ATPase activity of Eg5 (IC 50 = 140 nM). Induces mitotic arrest in HeLa cells with an IC 50 of 700 nM. Displays antitumor activity.

Synthesis

Triphenylmethanol (3.3 g, 12.7 mmol) and L-cysteine hydrochloride (2 g, 12.7 mmol) were reacted in 25 mL of trifluoroacetic acid (TFA). The mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the mixture was cooled to 0 °C, followed by the slow addition of 4 N sodium hydroxide solution and ether (40 mL) to adjust the pH to 4-5. Next, 10% aqueous sodium acetate was added to further adjust the pH to 5-6. The precipitate precipitated from the reaction mixture was collected by filtration, washed with fresh ether, and dried to afford S-trityl-L-cysteine (5 g, 98% yield). The structure of the product was confirmed by 1H NMR (DMSO-d6): δ 2.35-2.61 (m, 2H, CH2), 2.85-2.98 (m, 1H, CH), 7.2-7.45 (m, 15H, triphenylmethyl-L-H).MALDI-TOF MS analysis showed m/z 364.7 [M + H]+, which is in agreement with the theoretical C22H21NO2S molecular weight (363.47).

storage

Store at +4°C

References

[1] S. DEBONIS. In vitro screening for inhibitors of the human mitotic kinesin Eg5 with antimitotic and antitumor activities.[J]. Molecular Cancer Therapeutics, 2004, 3 9 1: 1079-1090. DOI:10.1158/1535-7163.1079.3.9
[2] SÉBASTIEN BRIER. Identification of the Protein Binding Region of S-Trityl-l-cysteine, a New Potent Inhibitor of the Mitotic Kinesin Eg5†[J]. Biochemistry Biochemistry, 2004, 43 41: 13072-13082. DOI:10.1021/bi049264e
[3] DIMITRIOS A SKOUFIAS. S-trityl-L-cysteine is a reversible, tight binding inhibitor of the human kinesin Eg5 that specifically blocks mitotic progression.[J]. The Journal of Biological Chemistry, 2006, 281 26: 17559-17569. DOI:10.1074/jbc.m511735200

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