トシルフェニルアラニルクロロメチルケトン
- 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
Wikipedia preview
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)
[Wiki en表示]
Tosyl phenylalanyl chloromethyl ketone
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Identifiers |
CAS Number
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402-71-1 Y |
3D model (Jmol) |
Interactive image |
ChemSpider |
388718 |
ECHA InfoCard |
100.006.323 |
MeSH |
Tosylphenylalanyl+Chloromethyl+Ketone |
PubChem |
439647 |
InChI
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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
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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
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SMILES
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Cc1ccc(cc1)S(=O)(=O)N[C@@H](Cc2ccccc2)C(=O)CCl
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Properties |
Chemical formula
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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).
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Y verify (what is YN ?) |
Infobox references |
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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.
UpToDate Contents
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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 Links
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- Medical Definition of Tosylphenylalanyl chloromethyl ketone 1. An inhibitor of serine proteinases. Acts as alkylating agent and is known to interfere with the translation process. Pharmacological action: alkylating agents, protein ...
Related Pictures
![Tosylphenylalanyl Chloromethyl Ketone](https://1mg.info/0/c/6/0138.jpg)
![, tosylphenylalanyl; chloromethyl ketone](https://1mg.info/0/c/6/0139.jpg)
![amino 3-chloro Molecules@GNU-Darwin.org](https://1mg.info/0/c/6/0140.jpg)
![Tosylphenylalanyl Chloromethyl Ketone](https://1mg.info/0/c/6/0141.jpg)
![Tosylphenylalanyl+Chloromethyl+Ketone](https://1mg.info/0/c/6/0142.jpg)
★リンクテーブル★
[★]
- 英
- tosylphenylalanyl chloromethyl ketone、TPCK