S-Trityl-L-cysteine

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
S-Trityl-L-cysteine Structure
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.
pka2.22±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 Reference2799-07-7(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 22-24/25
WGK Germany 3
RTECS AY7710000
HS Code 29309090
Toxicitydog,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 Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
S-Trityl-L-cysteine Usage And Synthesis
DescriptionS-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 Propertiesalmost white to light yellow granular powder
UsesA 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.
DefinitionChEBI: (2R)-2-amino-3-[(triphenylmethyl)thio]propanoic acid is a benzenoid aromatic compound.
Biological ActivityPotent, 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.
storageStore at +4°C
References1) 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
S-Trityl-L-cysteine Preparation Products And Raw materials
FMOC-CYS(DMT)-OH H-PEN(TRT)-OH N-FMOC-S-TRITYL-L-CYSTEINE,N-ALPHA-FMOC-S-TRITYL-L-CYSTEINE,Nα-Fmoc-S-trityl-L-cysteine ,S-TRITYL-L-CYSTEINE, N-FMOC PROTECTED S-Carboxymethyl-L-cysteine Toluene (-)-2-[METHYLAMINO]-1-PHENYLPROPANE FMOC-CYS(TRT)-OME TRITYL-S-TRITYL-L-CYSTEINE DIETHYLAMMONIUM SALT,N-ALPHA-TRITYL-S-TRITYL-L-CYSTEINE DIETHYLAMINE SALT Trityl candesartan cilexetil Fmoc-S-Trityl-L-penicillamine L-Cystine FMOC-CYS(4-METHOXYTRITYL)-OH S-Trityl-L-cysteine L-Cysteine p-Toluic acid TRT-CYS(TRT)-OH Triphenylmethyl Chloride 2-CLTRT RESIN-CYS(MMT)-OBT

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