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S-Trityl-L-cysteine

CAS No.
2799-07-7
Chemical Name:
S-Trityl-L-cysteine
Synonyms
H-CYS(TRT)-OH;Dimethyl 5-bromopyridine-2,3-dicarboxylate;L-Cys(Trt)-OH;H-L-Cys(Trt)-OH;S-Tritylcysteine;H-Cys(Trt)-OH (Cys of Animal Origin);NSC 83265;EG5 INHIBITOR II;CYSTEINE(TRT)-OH;TRITYL-L-CYSTEINE
CBNumber:
CB7164332
Molecular Formula:
C22H21NO2S
Molecular Weight:
363.47
MDL Number:
MFCD00002611
MOL File:
2799-07-7.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-07-14 16:49:18

S-Trityl-L-cysteine 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.
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)
UNSPSC Code 12352209
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312+P330-P501-P301+P312a-P330-P501a
PPE dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes  Xn
Risk Statements  22
Safety Statements  22-24/25
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,
NFPA 704
1
1 0

S-Trityl-L-cysteine price More Price(93)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 164739 (+)-S-Trityl-L-cysteine 97% 2799-07-7 5g $216 2026-04-30 Buy
TCI Chemical T2522 S-Trityl-L-cysteine >95.0%(T) 2799-07-7 5g $53 2026-04-30 Buy
Cayman Chemical 23236 S-trityl-L-Cysteine ≥98% 2799-07-7 1g $28 2026-04-30 Buy
Cayman Chemical 23236 S-trityl-L-Cysteine ≥98% 2799-07-7 5g $85 2026-04-30 Buy
Cayman Chemical 23236 S-trityl-L-Cysteine ≥98% 2799-07-7 10g $154 2026-04-30 Buy
Product number Packaging Price Buy
164739 5g $216 Buy
T2522 5g $53 Buy
23236 1g $28 Buy
23236 5g $85 Buy
23236 10g $154 Buy

S-Trityl-L-cysteine Chemical Properties, Uses, Production

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

76-84-6

L-Cysteine monohydrochloride

52-89-1

S-Trityl-L-cysteine

2799-07-7

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

S-Trityl-L-cysteine Preparation Products And Raw materials

Global Suppliers ( 295)
Supplier Tel Email Country ProdList Advantage
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
Meryer (Shanghai) Chemical Technology Co., Ltd. 4006356688 18621169109 market03@meryer.com China 40202 62
3B Pharmachem (Wuhan) International Co.,Ltd. 18930552037 3bsc@sina.com China 15813 69
Alfa Aesar 400-6106006 saleschina@alfa-asia.com China 30103 84
TCI (Shanghai) Development Co., Ltd. 021-67121386 Sales-CN@TCIchemicals.com China 24512 81
Energy Chemical 400-0056266 sales8178@energy-chemical.com China 44850 61
GL Biochem (Shanghai) Ltd 21-61263452 13641803416 ymbetter@glbiochem.com China 9981 64
Capot Chemical Co., Ltd +86 (0) 571 85 58 67 18 China 18187 66
Shanghai Sinch Parmaceuticals Tech. Co. Ltd. +86-21-54098501 sales@sinch.com.cn China 11592 64
VDM Biochemicals 0330-2528181 sales@vdmbio.com United States 510 64

View Latest Price from S-Trityl-L-cysteine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
S-trityl-L-Cysteine pictures 2026-07-14 S-trityl-L-Cysteine
2799-07-7
$31.00-81.00 97.08% 10g TargetMol Chemicals Inc.
(+)-S-Trityl-L-cysteine 97% pictures 2021-07-02 (+)-S-Trityl-L-cysteine 97%
2799-07-7
$10.00-15.00 1KG 99%+ HPLC Zhuozhou Wenxi import and Export Co., Ltd
S-Trityl-L-cysteine pictures 2019-07-06 S-Trityl-L-cysteine
2799-07-7
$1.00 1KG 99% 20kg Career Henan Chemical Co
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) S-Trityl-L-cysteine≥ 98% (HPLC) CYSTEINE(TRT)-OH EG5 INHIBITOR II NSC 83265 S-(TRIPHENYLMETHYL)-L-CYSTEINE (+)-S-TRITYL-L-CYSTEINE (2R)-2-ammonio-3-[(triphenylmethyl)thio]propanoate (2R)-2-amino-3-[(triphenylmethyl)sulfanyl]propanoic acid S-TRITYL-L-CYSTEINE TRITYL-L-CYSTEINE S-TRITYL-L-CYSTEINE CRYSTALLINE (+)-S-TRITYL-L-CYSTEINE 97% L-Cysteine, -3,3-D2-S-Trityl (R)-2-Amino-3-(tritylthio)propionic acid (R)-S-Tritylcysteine S-Trityl-(R)-cycteine S-Tritylcysteine S-TRITYL-L-CYSTEINE extrapure (2R)-2-AMino-3-[(triphenylMethyl)thio]propanoic Acid S-Trityl-(R)-cysteine Tritylthioalanine S-Trityl-L-cysteine,97% (R)-2-AMino-3-tritylsulfanyl-propionic acid L-CYSTEINE, S-TRITYL L-Cysteine, S-(triphenylmethyl)- S-Trityl-L-cysteine USP/EP/BP S-Tritylcysteine,Kinesin,StritylLCysteine,Apoptosis,328542,inhibit,cell cycle arrest,Inhibitor,NSC 83265,antitumor activities,NSC-83265,ATPase activity,kinesin Eg5,NSC83265,S trityl L Cysteine Tritylthioalanine (H-Cys(Trt)-OH) Impurity IIa-2 (S-triphenylmethylL-cysteine) S-Trityl-cysteine, kinesin Eg5 inhibitor S-trityl-L-Cysteine, 10 mM in DMSO (+)-S-Trityl-L-cysteine S-Trityl-L-cysteine - animal origin (2R)-2-azaniumyl-3-tritylsulfanylpropanoate Dimethyl 5-bromopyridine-2,3-dicarboxylate H-CYS(TRT)-OH H-L-Cys(Trt)-OH L-Cys(Trt)-OH 2799-07-7 2799-7-7 279-07-7 2799-07-07 7/7/2799 2799/7/7 328542 C6H53CSCD2CHNH2COOH C6H53CSCH2CHNH2CO2H Specialty Synthesis Peptide Synthesis Cysteine/Cystine CARBOXYLIC ACID Amino Acid Derivatives Cell Cycle Regulation