| Identification | More | [Name]
S-Trityl-L-cysteine | [CAS]
2799-07-7 | [Synonyms]
CYSTEINE(TRT)-OH
EG5 INHIBITOR II
H-CYS(TRT)-OH
NSC 83265
S-(TRIPHENYLMETHYL)-L-CYSTEINE
(+)-S-TRITYL-L-CYSTEINE
S-TRITYL-L-CYSTEINE
TRITYL-L-CYSTEINE
3-(tritylthio)-l-alanin
3-tritylthio-l-alanine
s-(triphenylmethyl)-l-cystein
S-TRITYL-L-CYSTEINE CRYSTALLINE
(+)-S-TRITYL-L-CYSTEINE 97%
L-Cysteine,-3,3-D2-S-Trityl
Dimethyl 5-bromopyridine-2,3-dicarboxylate
H-L-Cys(Trt)-OH
S-TRITYL-L-CYSTEINE extrapure
(R)-2-Amino-3-(tritylthio)propionic acid
(R)-S-Tritylcysteine
S-Trityl-(R)-cycteine | [EINECS(EC#)]
218-195-8 | [Molecular Formula]
C22H21NO2S | [MDL Number]
MFCD00002611 | [Molecular Weight]
363.47 | [MOL File]
2799-07-7.mol |
| Chemical Properties | Back Directory | [Appearance]
almost white to light yellow granular powder | [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. ]
-20°C | [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 Rotation]
[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. | [Major Application]
peptide synthesis | [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 Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302 | [Precautionary statements ]
P264-P270-P301+P312+P330-P501-P301+P312a-P330-P501a | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
AY7710000
| [HS Code ]
29309090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral | [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, |
| Hazard Information | Back Directory | [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. | [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. | [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) 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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| Company Name: |
J & K SCIENTIFIC LTD.
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18210857532 18210857532 |
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https://www.jkchemical.com |
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Alfa Aesar
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400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
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400-0056266 |
| Website: |
www.energy-chemical.com |
| Company Name: |
Maya High Purity Chemicals
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+86 (573) 82222445 (0)18006601000 452520369 |
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