Tosyl-L-lysine-chloromethyl-ketone
An inhibitor of serine endopeptidases. Acts as an alkylating agent and is known to interfere with the translation process. also inhibits Trypsine
General
Type : Ketone,Peptide,Sulfur Compound,Sulfonamide,Benzenesulfonamide
Chemical_Nomenclature : N-[(3S)-7-amino-1-chloro-2-oxoheptan-3-yl]-4-methylbenzenesulfonamide
Canonical SMILES : CC1=CC=C(C=C1)S(=O)(=O)NC(CCCCN)C(=O)CCl
InChI : InChI=1S\/C14H21ClN2O3S\/c1-11-5-7-12(8-6-11)21(19,20)17-13(14(18)10-15)4-2-3-9-16\/h5-8,13,17H,2-4,9-10,16H2,1H3\/t13-\/m0\/s1
InChIKey : RDFCSSHDJSZMTQ-ZDUSSCGKSA-N
Other name(s) : Tos-Lys-CH2Cl,Tosyl-L-lysine chloromethyl ketone,TLCK,TCK,Tosyllysyl chloromethyl ketone,N-alpha-p-Tosyl-L-lysine chloromethyl ketone,TCK\/PRD_000459,N-[(1S)-5-amino-1-(chloroacetyl)pentyl]-4-methylbenzenesulfonamide,CHEMBL466465,CHEBI:9640,SCHEMBL200247,ZINC1532775
MW : 332.8
Formula : C14H21ClN2O3S
CAS_number : 2364-87-6
PubChem : 73094
UniChem : RDFCSSHDJSZMTQ-ZDUSSCGKSA-N
IUPHAR :
Wikipedia :
Target
Families : Tosyl-L-lysine-chloromethyl-ketone ligand of proteins in family: Carb_B_Bacteria || BCHE || S9N_PREPL_Peptidase_S9
Stucture :
Protein : entcl-PRBA || human-BCHE || 9gamm-b3vi58
References (7)
| Title : Crystal Structure of Inhibitor-Bound Bacterial Oligopeptidase B in the Closed State: Similarity and Difference between Protozoan and Bacterial Enzymes - Petrenko_2023_Int.J.Mol.Sci_24_2286 |
| Author(s) : Petrenko DE , Karlinsky DM , Gordeeva VD , Arapidi GP , Britikova EV , Britikov VV , Nikolaeva AY , Boyko KM , Timofeev VI , Kuranova IP , Mikhailova AG , Bocharov EV , Rakitina TV |
| Ref : Int J Mol Sci , 24 : , 2023 |
| Abstract : Petrenko_2023_Int.J.Mol.Sci_24_2286 |
| ESTHER : Petrenko_2023_Int.J.Mol.Sci_24_2286 |
| PubMedSearch : Petrenko_2023_Int.J.Mol.Sci_24_2286 |
| PubMedID: 36768612 |
| Gene_locus related to this paper: 9gamm-b3vi58 |
| Title : The Crystal Structure of Nalpha-p-tosyl-lysyl Chloromethylketone-Bound Oligopeptidase B from Serratia Proteamaculans Revealed a New Type of Inhibitor Binding. - Timofeev_2021_Crystals_11_1438 |
| Author(s) : Timofeev VI , Petrenko DE , Agapova YK , Vlaskina AV , Karlinsky DM , Mikhailova AG , Kuranova IP , Rakitina TV |
| Ref : Crystals , 11 :1438 , 2021 |
| Abstract : Timofeev_2021_Crystals_11_1438 |
| ESTHER : Timofeev_2021_Crystals_11_1438 |
| PubMedSearch : Timofeev_2021_Crystals_11_1438 |
| PubMedID: |
| Gene_locus related to this paper: 9gamm-b3vi58 |
| Title : Purification and subcellular localization of a secreted 75 kDa Trypanosoma cruzi serine oligopeptidase - da Silva-Lopez_2008_Acta.Trop_107_159 |
| Author(s) : da Silva-Lopez RE , Morgado-Diaz JA , dos Santos PT , Giovanni-De-Simone S |
| Ref : Acta Trop , 107 :159 , 2008 |
| Abstract : da Silva-Lopez_2008_Acta.Trop_107_159 |
| ESTHER : da Silva-Lopez_2008_Acta.Trop_107_159 |
| PubMedSearch : da Silva-Lopez_2008_Acta.Trop_107_159 |
| PubMedID: 18599007 |
| Title : Do alkylating agents modify the histidine residue of the desensitized butyrylcholinesterase? - Cokugras_2004_Protein.J_23_495 |
| Author(s) : Cokugras AN , Cengiz D , Tezcan EF |
| Ref : Protein J , 23 :495 , 2004 |
| Abstract : Cokugras_2004_Protein.J_23_495 |
| ESTHER : Cokugras_2004_Protein.J_23_495 |
| PubMedSearch : Cokugras_2004_Protein.J_23_495 |
| PubMedID: 15648971 |
| Title : Purification and characterization of PrbA, a new esterase from Enterobacter cloacae hydrolyzing the esters of 4-hydroxybenzoic acid (parabens) - Valkova_2003_J.Biol.Chem_278_12779 |
| Author(s) : Valkova N , Lepine F , Labrie L , Dupont M , Beaudet R |
| Ref : Journal of Biological Chemistry , 278 :12779 , 2003 |
| Abstract : Valkova_2003_J.Biol.Chem_278_12779 |
| ESTHER : Valkova_2003_J.Biol.Chem_278_12779 |
| PubMedSearch : Valkova_2003_J.Biol.Chem_278_12779 |
| PubMedID: 12556461 |
| Gene_locus related to this paper: entcl-PRBA |
| Title : Protective action of the serine protease inhibitor N-tosyl-L-lysine chloromethyl ketone (TLCK) against acute soman poisoning - Cowan_2001_J.Appl.Toxicol_21_293 |
| Author(s) : Cowan FM , Broomfield CA , Lenz DE , Shih TM |
| Ref : J Appl Toxicol , 21 :293 , 2001 |
| Abstract : Cowan_2001_J.Appl.Toxicol_21_293 |
| ESTHER : Cowan_2001_J.Appl.Toxicol_21_293 |
| PubMedSearch : Cowan_2001_J.Appl.Toxicol_21_293 |
| PubMedID: 11481662 |
| Title : Histidine modification of human serum butyrylcholinesterase - Cengiz_1997_Biochem.Mol.Med_61_52 |
| Author(s) : Cengiz D , Cokugras AN , Kilinc K , Tezcan EF |
| Ref : Biochemical & Molecular Medicine , 61 :52 , 1997 |
| Abstract : Cengiz_1997_Biochem.Mol.Med_61_52 |
| ESTHER : Cengiz_1997_Biochem.Mol.Med_61_52 |
| PubMedSearch : Cengiz_1997_Biochem.Mol.Med_61_52 |
| PubMedID: 9232197 |