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164739

(+)-S-Trityl-L-cysteine

Name: (+)-<I>S</I>-Trityl-<SC>L</SC>-cysteine
Brand: ALDRICH

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

UNSPSC Code:

12352209

eCl@ss:

32160406

PubChem Substance ID:

24850097

NACRES:

NA.22

Beilstein/REAXYS Number:

2339626

MDL number:

MFCD00002611

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Properties

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

Description

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

GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Molecular dissection of the inhibitor binding pocket of mitotic kinesin Eg5 reveals mutants that confer resistance to antimitotic agents.

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

Optimized S-trityl-L-cysteine-based inhibitors of kinesin spindle protein with potent in vivo antitumor activity in lung cancer xenograft models.

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

Proteome analysis of apoptosis signaling by S-trityl-L-cysteine, a potent reversible inhibitor of human mitotic kinesin Eg5.

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

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Global Trade Item Number

SKU	GTIN
S1515-.2ML	04061837724305
S3396-.2ML	04061837724459
164739-5G	04061838748294