(+)-S-Trityl-L-cysteine

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

97%, for peptide synthesis

Sinónimos:

S-Trityl-L-cysteine

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Fórmula lineal:

(C₆H₅)₃CSCH₂CH(NH₂)CO₂H

Número CAS:

2799-07-7

Peso molecular:

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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Nombre del producto

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

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

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

Quality Level

100

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Este artículo	459313	C2196	A7772
Sigma-Aldrich 164739 (+)-S-Trityl-L-cysteine	Sigma-Aldrich 459313 Boc-Cys(Trt)-OH	Sigma-Aldrich C2196 L-Cysteine S-sulfate	Sigma-Aldrich A7772 S-(5′-Adenosyl)-L-cysteine
assay 97%	assay 97%	assay ≥98% (TLC)	assay >98% (TLC)
mp 182-183 °C (dec.) (lit.)	mp 143-146 °C (lit.)	mp -	mp -
Quality Level 100	Quality Level 200	Quality Level 200	Quality Level 200
optical activity [α]25/D +115°, c = 0.8 in 0.04 M ethanolic HCl	optical activity [α]20/D +27.5°, c = 1 in ethanol	optical activity -	optical activity -
reaction suitability reaction type: solution phase peptide synthesis	reaction suitability reaction type: Boc solid-phase peptide synthesis	reaction suitability -	reaction suitability -
application(s) peptide synthesis	application(s) peptide synthesis	application(s) -	application(s) -

Application

(+)-S-Trityl-L-cysteine, a non-natural, sulfur-containing amino acid is commonly used as a reagent in solution phase peptide synthesis (SPPS).[1][2] 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.[3]

pictograms

GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Clase de almacenamiento

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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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)

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

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

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

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