関: TPCK

WordNet

any of a class of organic compounds having a carbonyl group linked to a carbon atom in each of two hydrocarbon radicals

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/02/20 09:25:06」(JST)

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Tosyl phenylalanyl chloromethyl ketone (TPCK) is a protease inhibitor. Its structural formula is 1-chloro-3-tosylamido-4-phenyl-2-butanone.

Uses

TPCK is an irreversible inhibitor of chymotrypsin. Also inhibits some cysteine proteases such as caspase, papain, bromelain or ficin.^[1] It does not inhibit trypsin or zymogens.

TPCK is observed covalently bound in the active site of Caspase 3 in the crystal structure of the complex solved in 2010.^[2] The chloromethyl group reacts with the active site cysteine to form a covalent bond with the loss of the chlorine.

TPCK is chosen for the chemical labelling of active histidine in enzyme analysis. The phenylalanine moiety is bound to the enzyme because of specificity for aromatic amino acid residues at the active site (as in chymotrypsin, in which it binds to the Histidine-57 residue in the active site).^[3]

References

^ Focus Biomolecules Catalog # 10-2290 TPCK. [1], Retrieved on May 23. 2013.
^ Ganesan et al. Acta Crystallogr F v67 p 842. PDB Entry 2xyg
^ Farrell, Shawn O.; Campbell, Mary K. (2006). Biochemistry. Australia: Thomson Brooks/Cole. p. 160. ISBN 0-534-39499-X.

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English Journal

Serine protease inhibitors interact with IFN-γ through up-regulation of FasR; a novel therapeutic strategy against cancer.

Shadrin N1, Shapira MG1, Khalfin B2, Uppalapati L3, Parola AH4, Nathan I5.
Experimental cell research.Exp Cell Res.2015 Jan 15;330(2):233-9. doi: 10.1016/j.yexcr.2014.11.005. Epub 2014 Nov 18.
Among the many immunomodulatory and anti-tumor activities, IFN-γ up-regulates tumor cell death mediated by Fas receptor (FasR). Our and several other studies have demonstrated the involvement of trypsin-like proteases (TLPs) in the mode of action of IFN-γ. In the present study, we tried to unravel
PMID 25449698

Protease in sturgeon sperm and the effects of protease inhibitors on sperm motility and velocity.

Alavi SM1, Postlerová-Maňásková P, Hatef A, Pšenička M, Pěknicová J, Inaba K, Ciereszko A, Linhart O.
Fish physiology and biochemistry.Fish Physiol Biochem.2014 Oct;40(5):1393-8. doi: 10.1007/s10695-014-9933-8. Epub 2014 Mar 28.
In mammals, proteases are present in sperm acrosome and play key role in fertilization. Sturgeon sperm has an acrosome, but its physiology, biochemistry, and potential role in fertilization are unknown. In the present study, we have observed high protease activity in acidic extract of intact sperm c
PMID 24677048

The cellular inhibitor of apoptosis protein-2 is a possible target of novel treatment for endometriosis.

Taniguchi F1, Higaki H, Izawa M, Azuma Y, Hirakawa E, Deura I, Iwabe T, Hata K, Harada T.
American journal of reproductive immunology (New York, N.Y. : 1989).Am J Reprod Immunol.2014 Mar;71(3):278-85. doi: 10.1111/aji.12193. Epub 2014 Jan 2.
PROBLEM: How is the tumor necrosis factor (TNF) α-induced inhibitor of apoptosis (IAP) protein expression in endometriotic stromal cells (ESCs) involved in cell viability and signaling pathways METHOD OF STUDY: Endometriotic stromal cells were isolated from ovarian chocolate cysts in 20 patients wh
PMID 24382102

Japanese Journal

ATP-Induced Dynamic Fluorescence Changes of a N-(p-(2-Benzimidazolyl)Phenyl)maleimide Probe at Cys241 in the .ALPHA.-Chain of Pig Stomach H+,K+-ATPase.

Eguchi Hiroaki,Kaya Shunji,Shimada Akira,Ootomo Yuka,Nomoto Ken,Kikuchi Miki,Usida Yoshihiko,Taniguchi Kazuya
The Journal of Biochemistry 122(3), 659-665, 1997
… Tosylphenylalanyl chloromethyl ketone-trypsin treatment of the modified preparations, which showed an about 1% decrease in BIPM fluorescence accompanying phosphorylation, gave one major fluorescent peptide peak on reverse-phase chromatography. …
NAID 130003533264

States of Amino Acid Residues in Proteins:XXIV. Fluorescence of 3-Benzyl-4-methyl-7-diethylaminocoumarin in the Presence of α-Chymotrypsin and Its Derivatives

NISHIMURA Yoshihisa,TAKENAKA Osamu,SHIBATA Kazuo
The Journal of Biochemistry 70(2), 293-299, 1971
… 5] or its inactive forms such as chymotrypsinogen, alkali-denatured α-chymotrypsin, N-tosylphenylalanyl chloromethyl ketone (TPCK)-modified chymotrypsin and diisopropylfluorophosphate (DIP)-modified chymotrypsin. …
NAID 130003538625

Related Pictures

★リンクテーブル★

リンク元	「トシルフェニルアラニルクロロメチルケトン」

「トシルフェニルアラニルクロロメチルケトン」

Tosyl phenylalanyl chloromethyl ketone
Identifiers
CAS Number	402-71-1
3D model (Jmol)	Interactive image
ChemSpider	388718
ECHA InfoCard	100.006.323
MeSH	Tosylphenylalanyl+Chloromethyl+Ketone
PubChem	439647
	InChI 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 Key: MQUQNUAYKLCRME-INIZCTEOSA-N ; InChI=1/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 Key: MQUQNUAYKLCRME-INIZCTEOBY ;
	SMILES Cc1ccc(cc1)S(=O)(=O)N[C@@H](Cc2ccccc2)C(=O)CCl ;
Properties
Chemical formula	C17H18ClNO3S
Molar mass	351.848 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

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英: tosylphenylalanyl chloromethyl ketone、TPCK

[1] Focus Biomolecules Catalog # 10-2290 TPCK. [1], Retrieved on May 23. 2013.

[2] Ganesan et al. Acta Crystallogr F v67 p 842. PDB Entry 2xyg

[isbn0-534-39499-x-3] Farrell, Shawn O.; Campbell, Mary K. (2006). Biochemistry. Australia: Thomson Brooks/Cole. p. 160. ISBN 0-534-39499-X.

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tosylphenylalanyl chloromethyl ketone