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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
Tocris Bioscience
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Leancare Ltd.
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CARBONE SCIENTIFIC CO.,LTD
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Fluorochem Ltd.
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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
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  • 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
  • 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
  • (+)-<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