S-Trityl-L-cysteine

Product Name: 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;H-L-Cys(Trt)-OH;S-Tritylcysteine;H-Cys(Trt)-OH (Cys of Animal Origin);NSC 83265;L-Cys(Trt)-OH;EG5 INHIBITOR II;CYSTEINE(TRT)-OH;TRITYL-L-CYSTEINE
CBNumber: CB7164332
Molecular Formula: C22H21NO2S
Formula Weight: 363.47
MOL File: 2799-07-7.mol

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S-Trityl-L-cysteine Property

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)

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Safety

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,

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 164739
Product name: (+)-S-Trityl-L-cysteine
Purity: 97%
Packaging: 5g
Price: $203
Updated: 2025/07/31

TCI Chemical

Product number: T2522
Product name: S-Trityl-L-cysteine
Purity: >95.0%(T)
Packaging: 5g
Price: $49
Updated: 2025/07/31

Cayman Chemical

Product number: 23236
Product name: S-trityl-L-Cysteine
Purity: ≥98%
Packaging: 1g
Price: $25
Updated: 2024/03/01

Cayman Chemical

Product number: 23236
Product name: S-trityl-L-Cysteine
Purity: ≥98%
Packaging: 5g
Price: $77
Updated: 2024/03/01

Cayman Chemical

Product number: 23236
Product name: S-trityl-L-Cysteine
Purity: ≥98%
Packaging: 10g
Price: $140
Updated: 2024/03/01

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S-Trityl-L-cysteine Chemical Properties,Usage,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

76-84-6

52-89-1

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

Raw materials

Preparation Products

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S-Trityl-L-cysteine Suppliers

Belgium 1 Canada 1 China 196 Europe 1 Germany 5 India 7 Italy 1 Japan 7 South Korea 1 Switzerland 3 The Netherlands 1 United Kingdom 9 United States 56 Global 289

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

Zhuozhou Wenxi import and Export Co., Ltd

Product: (+)-S-Trityl-L-cysteine 97% 2799-07-7
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-06-27

Career Henan Chemical Co

Product: S-Trityl-L-cysteine 2799-07-7
Price: US $1.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 20kg
Release date: 2018-08-15

2799-07-7, S-Trityl-L-cysteineRelated Search:

Triphenylmethyl Chloride S-Carboxymethyl-L-cysteine p-Toluic acid L-Cysteine Trityl candesartan cilexetil L-Cystine H-L-Cys(Trt)-OtBu*HCl N-[S-Trityl-L-cysteinyl]glycine L-Phenylalanine Fmoc-L-glutamic acid FMOC-LYS-OH Di-tert-butyl dicarbonate D-Tyrosine Nalpha-Fmoc-L-tyrosine L-Leucine FMOC-b-Ala-OH 9-Fluorenemethanol S-TRITYL-L-CYSTEINE AMIDE HYDROCHLORIDE

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

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

Dimethyl 5-bromopyridine-2,3-dicarboxylate

H-L-Cys(Trt)-OH

(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

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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

(+)-<i>S</i>-Trityl-<sc>L</sc>-cysteine

S-Trityl-L-cysteine - animal origin

(2R)-2-azaniumyl-3-tritylsulfanylpropanoate

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