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164739

Sigma-Aldrich

(+)-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:
2799-07-7
Molecular Weight:
363.47
Beilstein:
2339626
MDL number:
MFCD00002611
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24850097
NACRES:
NA.22

product name

(+)-S-Trityl-L-cysteine, 97%

Quality Level

100

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

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV1857
MKCP9350
MKCG2675
MKCC9351
MKBZ3032V

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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)
Total synthesis of didmolamides A and B
You Shu-Li and Kelly JW
Tetrahedron Letters, 46(15), 2567-2570 (2005)
James A D Good et al.
Journal of medicinal chemistry, 56(5), 1878-1893 (2013-02-12)
The mitotic kinesin Eg5 is critical for the assembly of the mitotic spindle and is a promising chemotherapy target. Previously, we identified S-trityl-L-cysteine as a selective inhibitor of Eg5 and developed triphenylbutanamine analogues with improved potency, favorable drug-like properties, but
Frank Kozielski et al.
Proteomics, 8(2), 289-300 (2008-01-11)
Mitotic kinesins represent potential drug targets for anticancer chemotherapy. Inhibitors of different chemical classes have been identified that target human Eg5, a kinesin responsible for the establishment of the bipolar spindle. One potent Eg5 inhibitor is S-trityl-L-cysteine (STLC), which arrests
Sergey Tcherniuk et al.
Biochemical pharmacology, 79(6), 864-872 (2009-11-10)
The kinesin Eg5 plays an essential role in bipolar spindle formation. A variety of structurally diverse inhibitors of the human kinesin Eg5, including monastrol and STLC, share the same binding pocket on Eg5, composed by helix alpha2/loop L5, and helix
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