Nα-Tosyl-L-phenylalanine chloromethyl ketone
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Nα-Tosyl-L-phenylalanine chloromethyl ketone
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CAS No:
402-71-1
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Formula:
C17H18ClNO3S
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Chemical Name:
Nα-Tosyl-L-phenylalanine chloromethyl ketone
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Synonyms:
Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-;p-Toluenesulfonamide,N-[α-(chloroacetyl)phenethyl]-,L-;Benzenesulfonamide,N-[3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-,(S)-;N-[(1S)-3-Chloro-2-oxo-1-(phenylmethyl)propyl]-4-methylbenzenesulfonamide;N-Tosyl-L-phenylalanylchloromethane;Tosylphenylalanine chloromethyl ketone;L-1-Tosylamido-2-phenylethyl chloromethyl ketone;L-1-Chloro-4-phenyl-3-p-tolylsulfonamidobutan-2-one;Tosylphenylalanylchloromethane;α-N-Tosyl-L-phenylalanine chloromethyl ketone;L-Tolylsulfonylphenylalanyl chloromethyl ketone;Nα-Tosyl-L-phenylalanine chloromethyl ketone;N-Tosyl-L-phenylalaninechloromethane;L-1-Tosylamide-2-phenylethylchloromethyl ketone;N-α-Tosyl-L-phenylalanylchloromethane;L-1-Chloro-4-phenyl-3-toluene-p-sulfonamido-2-butanone;N-(p-Toluenesulfonyl)-L-phenylalanylchloromethane;L-1-Chloro-3-tosylamidyl-4-phenyl-2-butanone;N-Tosyl-L-phenylalanyl chloromethyl ketone;TPCK;N-Tosylphenylalanine chloromethyl ketone;(S)-N-(4-Chloro-3-oxo-1-phenylbutan-2-yl)-4-methylbenzenesulfonamide;130021-38-4
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CAS No:
Description
white crystalline powder
N-tosyl-L-phenylalanyl chloromethyl ketone is the N-tosyl derivative of L-phenylalanyl chloromethyl ketone. It has a role as an alkylating agent and a serine proteinase inhibitor. It is a sulfonamide and an alpha-chloroketone. It contains a L-phenylalanyl group.|An inhibitor of Serine Endopeptidases. Acts as alkylating agent and is known to interfere with the translation process.
Nα-Tosyl-L-phenylalanine chloromethyl ketone Basic Attributes
351.85
351.85
206-954-6
P598716LJT
727365
29350090
Characteristics
71.6
3.98
white powder
1.3±0.1 g/cm3
106-108 °C(lit.)
509.9±60.0 °C at 760 mmHg
262.2±32.9 °C
1.583
DMSO: >10 mg/mL stable for several months at 4°C.
−20°C
1.63E-10mmHg at 25°C
Safety Information
UN 3335
3
37/38-41
26-36
XT5613500
Xi
P261-P280-P305 + P351 + P338
H315-H318-H335
Drug Information
Exogenous or endogenous compounds which inhibit SERINE ENDOPEPTIDASES. (See all compounds classified as Serine Proteinase Inhibitors.)|Highly reactive chemicals that introduce alkyl radicals into biologically active molecules and thereby prevent their proper functioning. Many are used as antineoplastic agents, but most are very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. They have also been used as components in poison gases. (See all compounds classified as Alkylating Agents.)|Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)
Chloromethane, Tosylphenylalanyl
Nα-Tosyl-L-phenylalanine chloromethyl ketone Use and Manufacturing
N-α-Tosyl-L-phenylalanylchloromethane is a proteinase inhibitors with apoptotic function. Studies have shown that it induces caspase-dependent apoptosis in Epstein-Barr virus (EBV)-transformed human B cell lines with release of pro-apoptotic proteins from mitochondria. It also results in down-regulation of the anti-apoptotic proteins and caspase-dependent cleavage of two anti-apoptotic proteins. It promotes dephosphorylation of p53 on serine residues.
Benzenesulfonamide, N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-: INACTIVE
Computed Properties
Molecular Weight:351.8
XLogP3:3.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:7
Exact Mass:351.0695923
Monoisotopic Mass:351.0695923
Topological Polar Surface Area:71.6
Heavy Atom Count:23
Complexity:475
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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Nα-Tosyl-L-phenylalanine chloromethyl ketone
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