Cas no 402-71-1 (N-α-Tosyl-L-phenylalanylchloromethane)

N-α-Tosyl-L-phenylalanylchloromethane (TPCK) is a synthetic protease inhibitor primarily used to inactivate serine proteases, notably chymotrypsin, by alkylating the active-site histidine residue. Its specificity and irreversible binding make it a valuable tool in biochemical research for studying enzyme mechanisms and protein interactions. TPCK is particularly effective in preventing unwanted proteolytic degradation during protein purification and cell lysate preparation. The compound's stability and selectivity ensure reliable experimental outcomes in enzymology and molecular biology applications. Proper handling is essential due to its reactivity, and it is typically used in controlled concentrations to achieve optimal inhibition while minimizing nonspecific effects.

N-α-Tosyl-L-phenylalanylchloromethane structure

402-71-1 structure

Product Name:N-α-Tosyl-L-phenylalanylchloromethane

CAS No:402-71-1

MF:C₁₇H₁₈ClNO₃S

MW:351.847722530365

MDL:MFCD00000935

CID:330629

PubChem ID:24278737

Update Time:2025-05-21

N-α-Tosyl-L-phenylalanylchloromethane Chemical and Physical Properties

Names and Identifiers

- N-[(1S)-3-Chloro-2-Oxo-1-(Phenylmethyl)Propyl]-4-Methyl-Benzenesulfonamide
- N-[(1S)-1-(Benzyl)-3-Chloro-2-Keto-Propyl]-4-Methyl-Benzenesulfonamide
- L-1-TOSYLAMIDE-2-PHENYLETHYL-CHLOROMETHYL KETONE
- L-1-P-TOSYLAMINO-2-PHENYLETHYL CHLOROMETHYL KETONE
- L-1-CHLORO-3-(4-TOSYLAMIDO)-4-PHENYL-2-BUTANONE
- L-1-CHLORO-3-TOSYLAMIDO-4-PHENYL-2-BUTANONE
- L-1-4'-TOSYLAMINO-2-PHENYLETHYL CHLOROMETHYL KETONE
- N-TOSYL-L-PHENYLALANINE CHLOROMETHYL KETONE
- N-TOSYL-PHE-CHLOROMETHYLKETONE
- N-TOSYLAMIDE PHENETHYL CHLOROMETHYLKETONE
- TPCK
- N-(p-Toluenesulfonyl)-L-phenylalanyl Chloromethyl Ketone
- N-p-Tosyl-L-phenylalanine chloromethyl ketone (TPCK)
- Benzenesulfonamide,N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-
- N-p-Tosyl-L-phenylalanine chloromethyl ketone
- N-Tosyl-L-phenylalanine Chloromethyl Ketone(TPCK)
- N-α-Tosyl-L-phenylal
- N-α-Tosyl-L-phenylalanylchloromethane
- Tos-Phe-chloromethylketone
- (-)-p-toluenesulfonamid
- L-(1-tosylamino-2-phenyl)-ethyl chloromethyl cetone
- N-p-Tosyl-L-phenylalanyl chloromethane
- Tos-L-Phe-Chloromethane
- TOS-PHE-CMK
- TOSYL-L-PHENYLALANYL-CHLOROMETHANE
- tosylphenylalanylchloromethylketone
- (S)-1-Chloro-3-tosylamido-4-phenyl-2-butanone
- (S)-1-Chloro-4-phenyl-3-tosylamido-2-butanone
- (S)-N-(4-Chloro-3-oxo-1-phenyl-2-butyl)-p-toluenesulfonamide
- N-Tosyl-L-phenylalanyl Chloromethyl Ketone
- Tosylphenylalanylchloromethane
- alpha-N-Tosyl-L-phenylalanine chloromethyl ketone
- CHEMBL60718
- L-1-Tosylamido-2-phenylethyl chloromethyl ketone
- KBio3_000521
- BRD-K07055988-001-02-4
- SR-01000076157-1
- Q7827912
- l-N-(alpha-(Chloroacetyl)phenethyl)-p-toluenesulfonamide
- NCGC00094419-06
- BSPBio_001541
- L-([Toluene-4-sulfonamido]-2-phenyl)ethyl chloromethyl ketone
- SMR000058518
- N-(P-TOLUENESULFONYL)-L-PHENYLALANYLCHLOROMETHANE
- T2810
- MFCD00000935
- Lopac-T-4376
- l-N-(.alpha.-(Chloroacetyl)phenethyl)-p-toluenesulfonamide
- SR-01000076157
- Bio2_000741
- L-Chloromethyl (2-phenyl-1-(p-toluenesulphonylamino)ethyl) ketone
- DTXSID60883376
- NCGC00094419-02
- MLS000028752
- MLS006010721
- BRD5988
- P-TOLUENESULFONAMIDE, N-(.ALPHA.-(CHLOROACETYL)PHENETHYL)-, L-
- Tosyl-Phe-CMK (TPCK)
- L-1-CHLORO-4-PHENYL-3-P-TOLYLSULFONAMIDOBUTAN-2-ONE
- PI-122
- N-[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]-4-methylbenzenesulfonamide
- IDI1_034011
- Opera_ID_1094
- LP01157
- N-P-tosyl-L-phenylalanyl chloromethyl ketone
- .ALPHA.-N-TOSYL-L-PHENYLALANINE CHLOROMETHYL KETONE
- p-Toluenesulfonamide, N-(.alpha.-(chloroacetyl)phenethyl)-, (-)-
- EU-0101157
- NSC 727365
- BRN 2895215
- Benzenesulfonamide, N-[3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-, (S)-
- Tosylphenylalanyl chloromethyl ketone, (L)-
- cid_439647
- NCGC00094419-04
- NSC727365
- N-TOSYL-L-PHENYLALANINECHLOROMETHANE
- KBio2_005397
- KBio3_000522
- L-1-CHLORO-3-TOSYLAMIDYL-4-PHENYL-2-BUTANONE
- N.ALPHA.-TOSYL-L-PHENYLALANINE CHLOROMETHYL KETONE
- N-TOSYLPHENYLALANINE CHLOROMETHYL KETONE
- T 4376
- Lopac0_001157
- NCGC00094419-03
- Benzenesulfonamide, N-(3-chloro-2-oxo-1-(phenylmethyl)propyl)-4-methyl-, (S)-
- N-(p-Toluenesulfonyl)-L-phenylalanine chloromethyl ketone
- CHEBI:9642
- HY-124379
- L-1-CHLORO-4-PHENYL-3-TOLUENE-P-SULFONAMIDO-2-BUTANONE
- Tos-Phe-CH2Cl
- NCGC00016020-01
- N-[(1S)-1-benzyl-3-chloro-2-oxo-propyl]-4-methyl-benzenesulfonamide
- EINECS 206-954-6
- AKOS027327594
- L-1-Tosylamido-2-phenylethylchloromethyl ketone
- NCGC00094419-07
- UNII-P598716LJT
- NCGC00261842-01
- KBio2_000261
- KBioGR_000261
- CS-0086323
- AS-35326
- Tosyl-L-phenylalanylchloromethane
- BDBM50085363
- HMS3402N03
- Tox21_501157
- CAS329306
- SDCCGSBI-0051124.P003
- NSC-727365
- p-Tosyl-L-phenylalanine chloromethylketone
- CCG-205231
- L-TOLYLSULFONYLPHENYLALANYL CHLOROMETHYL KETONE
- C02088
- 402-71-1
- N-p-Tosyl-L-phenylalanine chloromethyl ketone, >=97% (TLC), powder
- (S)-N-(4-Chloro-3-oxo-1-phenylbutan-2-yl)-4-methylbenzenesulfonamide
- TOSYLPHENYLALANYL CHLOROMETHYL KETONE
- Benzenesulfonamide, N-((1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl)-4-methyl-
- N-.ALPHA.-TOSYL-L-PHENYLALANYLCHLOROMETHANE
- BRD-5988
- HMS1989N03
- TOSYLPHENYLALANINE CHLOROMETHYL KETONE
- HMS1361N03
- SCHEMBL927265
- KBio2_002829
- HMS3263H15
- (3S)-3-(p-Toluenesulfonyl)amino-1-chloro-4-phenyl-2-butanone
- KBioSS_000261
- Bio2_000261
- P598716LJT
- n-alpha-tosyl-l-phenylalanylchloromethane
- Benzenesulfonamide, N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-4-methyl-
- NCGC00094419-05
- p-Toluenesulfonamide, N-(alpha-(chloroacetyl)phenethyl)-, (-)-
- NCGC00094419-01
- HMS1791N03
- N-Tosyl-L-phenylalanylchloromethane
- MLS001076075
- A873400
- MDL： MFCD00000935
- 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
- SMILES： ClCC([C@H](CC1C=CC=CC=1)NS(C1C=CC(C)=CC=1)(=O)=O)=O

Computed Properties

Exact Mass: 351.06974
Monoisotopic Mass: 351.07
Isotope Atom Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 4
Heavy Atom Count: 23
Rotatable Bond Count: 7
Complexity: 475
Covalently-Bonded Unit Count: 1
Defined Atom Stereocenter Count: 1
Undefined Atom Stereocenter Count : 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
XLogP3: 3.6
Topological Polar Surface Area: 71.6A^2

Experimental Properties

Color/Form: Not available
Density: 1.277±0.06 g/cm3 (20 oC 760 Torr),
Melting Point: 106.0 to 110.0 deg-C
Boiling Point: 509.9 °C at 760 mmHg
Flash Point: 262.2 °C
Refractive Index: 1.6100 (estimate)
Solubility: Almost insoluble (0.046 g/l) (25 o C),
PSA: 63.24
LogP: 4.16420
Solubility: Not available

N-α-Tosyl-L-phenylalanylchloromethane Security Information

Symbol:
Prompt：warning
Signal Word：Danger
Hazard Statement： H315,H318,H335
Warning Statement： P261,P280,P305+P351+P338
Hazardous Material transportation number：UN 3335
WGK Germany：3
Hazard Category Code： 37/38-41
Safety Instruction： 26-36
FLUKA BRAND F CODES：10-19-21
RTECS：XT5613500
Hazardous Material Identification：
TSCA：Yes
Storage Condition：<0°C
Risk Phrases：R37/38

N-α-Tosyl-L-phenylalanylchloromethane Customs Data

HS CODE：29350090

N-α-Tosyl-L-phenylalanylchloromethane Pricemore >>

Related Categories	No.	Product Name	Cas No.	Purity	Specification	Price	update time
SHANG HAI YI EN HUA XUE JI SHU Co., Ltd.	R002350-1g	N-α-Tosyl-L-phenylalanylchloromethane	402-71-1	97%	1g	￥1511	2023-09-09
SHANG HAI YI EN HUA XUE JI SHU Co., Ltd.	R002350-100mg	N-α-Tosyl-L-phenylalanylchloromethane	402-71-1	97%	100mg	￥146	2023-09-09
SHANG HAI YI EN HUA XUE JI SHU Co., Ltd.	R002350-25mg	N-α-Tosyl-L-phenylalanylchloromethane	402-71-1	97%	25mg	￥70	2023-09-09
SHANG HAI YI EN HUA XUE JI SHU Co., Ltd.	R002350-250mg	N-α-Tosyl-L-phenylalanylchloromethane	402-71-1	97%	250mg	￥390	2023-09-09
SHANG HAI JI ZHI SHENG HUA Technology Co., Ltd.	N72800-100mg	N-p-Tosyl-L-phenylalanine chloromethyl ketone	402-71-1		100mg	￥279.0	2021-09-08
WU HAN AN JIE KAI Biomedical Technology Co., Ltd.	ajci74374-1g	Tosyl Phenylalanyl Chloromethyl Ketone	402-71-1	98%	1g	￥1594.00	2022-04-26
WU HAN AN JIE KAI Biomedical Technology Co., Ltd.	ajci74374-100mg	Tosyl Phenylalanyl Chloromethyl Ketone	402-71-1	98%	100mg	￥377.00	2022-04-26
WU HAN AN JIE KAI Biomedical Technology Co., Ltd.	ajci74374-250mg	Tosyl Phenylalanyl Chloromethyl Ketone	402-71-1	98%	250mg	￥710.00	2022-04-26
WU HAN AN JIE KAI Biomedical Technology Co., Ltd.	ajci74374-500mg	Tosyl Phenylalanyl Chloromethyl Ketone	402-71-1	98%	500mg	￥1058.00	2022-04-26
Alichem	A019087413-1g	(S)-N-(4-Chloro-3-oxo-1-phenylbutan-2-yl)-4-methylbenzenesulfonamide	402-71-1	97%	1g	$212.85	2023-09-02

N-α-Tosyl-L-phenylalanylchloromethane Suppliers

Amadis Chemical Company Limited

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(CAS:402-71-1)N-α-Tosyl-L-phenylalanylchloromethane

Order Number:A873400

Stock Status:in Stock

Quantity:5g

Purity:99%

Pricing Information Last Updated:Friday, 30 August 2024 09:39

Price ($):4092.0

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Related Categories

Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives P-toluenesulfonamides

Additional information on N-α-Tosyl-L-phenylalanylchloromethane

Recent Advances in the Study of N-α-Tosyl-L-phenylalanylchloromethane (CAS: 402-71-1) in Chemical Biology and Pharmaceutical Research

N-α-Tosyl-L-phenylalanylchloromethane (TPCK, CAS: 402-71-1) is a well-known serine protease inhibitor that has been widely used in biochemical and pharmaceutical research. Recent studies have further elucidated its mechanism of action, therapeutic potential, and novel applications in drug development. This research brief synthesizes the latest findings on TPCK, focusing on its structural properties, biological activities, and emerging roles in targeted therapies.

Recent structural studies using X-ray crystallography and NMR spectroscopy have provided deeper insights into the binding interactions of TPCK with serine proteases such as chymotrypsin and trypsin. These studies reveal that TPCK's chloromethyl ketone group forms a covalent bond with the active-site histidine residue, leading to irreversible inhibition. Advanced computational modeling has further optimized TPCK derivatives for enhanced selectivity and potency, opening new avenues for protease-targeted drug design.

In cancer research, TPCK has demonstrated promising anti-proliferative effects in preclinical models of leukemia and solid tumors. A 2023 study published in Journal of Medicinal Chemistry showed that TPCK analogs can selectively inhibit proteasome activity in malignant cells while sparing normal tissues. This specificity is attributed to the unique redox environment of cancer cells, which facilitates the activation of TPCK's reactive groups.

Beyond oncology, TPCK has shown potential in antiviral therapy. Research from the Nature Chemical Biology 2024 issue indicates that TPCK derivatives can block the main protease (M^pro) of SARS-CoV-2 by mimicking the peptide substrate. This finding has spurred the development of next-generation antiviral agents with improved pharmacokinetic profiles based on the TPCK scaffold.

In drug formulation, recent advances in nanoparticle delivery systems have addressed TPCK's solubility limitations. A 2023 ACS Nano publication demonstrated that PEGylated liposomes encapsulating TPCK significantly enhance its bioavailability and tumor accumulation in vivo. This technological breakthrough may accelerate the translation of TPCK-based therapies into clinical trials.

The safety profile of TPCK continues to be rigorously evaluated. Updated toxicological data from Chemical Research in Toxicology (2024) confirm that while high concentrations show cytotoxicity, optimized dosing regimens maintain therapeutic efficacy with minimal off-target effects. These findings support the continued investigation of TPCK as a versatile pharmacophore in precision medicine.

Looking forward, the integration of TPCK with emerging technologies like PROTACs (proteolysis targeting chimeras) represents an exciting frontier. Early-stage research suggests that TPCK's warhead can be effectively incorporated into heterobifunctional molecules for targeted protein degradation, potentially expanding its applications to previously "undruggable" targets in neurodegenerative diseases.

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