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S-Trityl-L-cysteine

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S-Trityl-L-cysteine Basic information

Product Name:
S-Trityl-L-cysteine
Synonyms:
  • 3-(tritylthio)-l-alanin
  • 3-tritylthio-l-alanine
  • s-(triphenylmethyl)-l-cystein
  • H-Cys(Trt)-OH (Cys of Animal Origin)
  • H-Cys(Trt)-OH (Cys of Non Animal Origin)
  • L-Cys(Trt)-OH
  • S-Trityl-L-cysteine≥ 98% (HPLC)
  • H-CYS(TRT)-OH
CAS:
2799-07-7
MF:
C22H21NO2S
MW:
363.47
EINECS:
218-195-8
Product Categories:
  • Cell Cycle Regulation
  • Amino Acid Derivatives
  • Amino Acids & Derivatives
  • Aromatics
  • Chiral Reagents
  • Enzyme substrates
  • Amino Acids Derivatives
  • Cysteine [Cys, C]
  • Amino Acids and Derivatives
  • Amino Acids 13C, 2H, 15N
Mol File:
2799-07-7.mol
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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.
CAS DataBase Reference
2799-07-7(CAS DataBase Reference)
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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

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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

(+)-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.

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.

Definition

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

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.

storage

Store at +4°C

References

1) DeBonis et al. (2004) In vitro screening for inhibitors of the human mitotic kinesin Eg5 with antimitotic and antitumour activities; Mol. Cancer Ther. 3 1079 2) Brier et al. (2004) Identification of the protein binding region of S-trityl-L-cysteine, a new potent inhibitor of mitotic kinesin Eg5; Biochemistry 43 13072 3) Skoufias et al. (2006) S-trityl-l-cysteine is a reversible, tight-binding inhibitor of the human kinesin eg5 that specifically blocks mitotic progression; J. Biol. Chem., 281 17559

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