Tos-Phe-chloromethylketone, CAS No. 402-71-1

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402-71-1

Catalog No. EBD2222027

CAS 402-71-1

Name Tos-Phe-chloromethylketone

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Basic Information

Synonyms: Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl- Tos-Phe-chloromethylketone L-chloromethyl(2-phenyl-1-(p-toluenesulphonylamino)ethyl)ketone BRN2895215 Benzenesulfonamide,N-(3-chloro-2-oxo-1-(phenylmethyl)propyl)-4-methyl-,(S)- L-1-Tosylamido-2-phenylethylchloromethylketone l-N-(alpha-(Chloroacetyl)phenethyl)-p-toluenesulfonamide Benzenesulfonamide,N-((1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl)-4-methyl- p-Toluenesulfonamide,N-(alpha-(chloroacetyl)phenethyl)-,(-)- N-(4-chloro-3-oxo-1-phenylbutan-2-yl)-4-methylbenzenesulfonamide N-[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]-4-methylbenzenesulfonamide

Molecular Formula: C17H18ClNO3S

Molecular Weight: 351.85

Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics Synthetic Chemistry > Basic Synthetic Reagents > Protecting and Deprotecting Reagents

Product Description:

N-(p-Tosyl)-L-phenylalanyl chloromethyl ketone (TPCK), with CAS number 402-71-1, is a synthetic chloromethyl ketone derivative of a tosyl-protected phenylalanine amino acid. It is a well-known, irreversible active-site-directed inhibitor of serine proteases, most notably chymotrypsin and chymotrypsin-like enzymes. The compound functions as an affinity label, where its phenylalanine side chain directs it to the substrate-binding pocket of the enzyme, and the reactive chloromethyl ketone group then alkylates a critical histidine residue in the active site, permanently inactivating the enzyme. TPCK is a classic tool compound in biochemical and cell biology research. It is extensively used to study the role of chymotrypsin-like proteases, such as the chymotrypsin-like activity of the proteasome, in various cellular processes including protein degradation, apoptosis, and inflammation signaling pathways. Its specificity, though not absolute, makes it valuable for probing enzyme mechanisms and function. Beyond its primary role as a protease inhibitor, the structural motif of TPCK incorporates a tosyl (p-toluenesulfonyl) protecting group on the amine functionality. This feature makes it relevant in synthetic peptide chemistry as a protected amino acid derivative or a specialized building block, particularly in contexts where chloromethyl ketone warheads are designed for activity-based protein profiling or inhibitor synthesis.

Physical Properties

Color: white

Melting Point: 106-108 °C(lit.)

Boiling Point: 509.9 °C at 760 mmHg

Flash Point: 262.2 °C

Density: 1.278 g/cm3

Storage: −20°C

Safety Information

Packing Level:

Hazard Category:

Transport Codes: 3335

Analytical Data

Appearance: white crystalline powder