164739
(+)-S-Trityl-L-cysteine
97%, for peptide synthesis
Synonym(s):
S-Trityl-L-cysteine
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About This Item
Linear Formula:
(C6H5)3CSCH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
363.47
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.22
Beilstein/REAXYS Number:
2339626
MDL number:
Product Name
(+)-S-Trityl-L-cysteine, 97%
assay
97%
optical activity
[α]25/D +115°, c = 0.8 in 0.04 M ethanolic HCl
reaction suitability
reaction type: solution phase peptide synthesis
mp
182-183 °C (dec.) (lit.)
application(s)
peptide synthesis
SMILES string
N[C@@H](CSC(c1ccccc1)(c2ccccc2)c3ccccc3)C(O)=O
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
InChI key
DLMYFMLKORXJPO-FQEVSTJZSA-N
Application
(+)-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.
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Design, synthesis, and evaluation of a novel prodrug, a S-trityl-l-cysteine derivative targeting kinesin spindle protein
Fukai R, et al.
European Journal of Medicinal Chemistry, 215, 113288-113288 (2021)
Synthesis and electrochemical studies of disubstituted ferrocene/dipeptide conjugates with sulfur-containing side chains
Scully CCG and Rutledge PJ
Tetrahedron, 66(30), 5653-5659 (2010)
Sébastien Brier et al.
Journal of molecular biology, 360(2), 360-376 (2006-06-20)
The mitotic kinesin Eg5 plays an essential role in establishing the bipolar spindle. Recently, several antimitotic inhibitors have been shown to share a common binding region on Eg5. Considering the importance of Eg5 as a potential drug target for cancer