Tos-Phe-chloromethylketone

Tos-Phe-chloromethylketone contains a tosyl (p-toluenesulfonyl) protected phenylalanine residue bearing a chloromethyl ketone electrophile, classifying it as an amino acid derivative designed for peptide-enzyme chemistry rather than a free amino acid. The molecule features an aromatic side chain consistent with the Phe amino acid, a ketone functional group adjacent to a chloromethyl moiety that provides a reactive handle for nucleophilic capture, and an amino-acid backbone functionality masked by the tosyl protecting group to control chemoselectivity during synthesis or labeling. In research workflows it is used as a substrate-mimetic or electrophilic inhibitor-like reagent in chemical biology and enzyme-substrate studies, where the chloromethyl ketone can be used to probe active-site interactions and to generate stable covalent adducts for analytical characterization.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP27087

CAS No:402-71-1

Synonyms/Alias:TPCK;Tos-Phe-CH2Cl;402-71-1;TOSYLPHENYLALANYLCHLOROMETHYLKETONE;N-Tosyl-L-phenylalanylchloromethylketone;N-p-Tosyl-L-phenylalaninechloromethylketone;N-Tosyl-L-phenylalaninechloromethylketone;CHEMBL60718;CHEBI:9642;MQUQNUAYKLCRME-INIZCTEOSA-N;L-1-Tosylamido-2-phenylethylchloromethylketone;N-[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]-4-methylbenzenesulfonamide;l-N-(alpha-(Chloroacetyl)phenethyl)-p-toluenesulfonamide;L-1-p-Tosylamino-2-phenylethylchloromethylketone;Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-;SMR000058518;Tosylphenylalanylchloromethylketone,(L)-;(S)-1-Chloro-3-tosylamido-4-phenyl-2-butanone;(S)-1-Chloro-4-phenyl-3-tosylamido-2-butanone;Lopac-T-4376;Lopac0_001157;BSPBio_001541;KBioGR_000261;KBioSS_000261;MLS000028752

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M.F/Formula
C17H18ClNO3S
M.W/Mr.
351.85
Size
1 g;5 g;
InChI
1S/C17H18ClNO3S/c1-13-7-9-15(10-8-13)23(21,22)19-16(17(20)12-18)11-14-5-3-2-4-6-14/h2-10,16,19H,11-12H2,1H3/t16-/m0/s1
InChI Key
MQUQNUAYKLCRME-INIZCTEOSA-N
Canonical SMILES
CC1=CC=C(C=C1)S(=O)(=O)NC(CC2=CC=CC=C2)C(=O)CCl

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