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3. Tosyl-L-lysine-chloromethyl-ketone

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

Target

Families : Tosyl-L-lysine-chloromethyl-ketone ligand of proteins in family
Carb_B_Bacteria BCHE S9N_PREPL_Peptidase_S9

Protein :
entcl-PRBA human-BCHE 9gamm-b3vi58

References (7)

1. Crystal Structure of Inhibitor-Bound Bacterial Oligopeptidase B in the Closed State: Similarity and Difference between Protozoan and Bacterial Enzymes

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

2. The Crystal Structure of Nalpha-p-tosyl-lysyl Chloromethylketone-Bound Oligopeptidase B from Serratia Proteamaculans Revealed a New Type of Inhibitor Binding.

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

3. Purification and subcellular localization of a secreted 75 kDa Trypanosoma cruzi serine oligopeptidase

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

4. Do alkylating agents modify the histidine residue of the desensitized butyrylcholinesterase?

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

5. Purification and characterization of PrbA, a new esterase from Enterobacter cloacae hydrolyzing the esters of 4-hydroxybenzoic acid (parabens)

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

6. Protective action of the serine protease inhibitor N-tosyl-L-lysine chloromethyl ketone (TLCK) against acute soman poisoning

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

7. Histidine modification of human serum butyrylcholinesterase

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

Array
(
    [id] => 2091
    [inhibitor] => Tosyl-L-lysine-chloromethyl-ketone
    [type] => Array
        (
            [0] => Ketone
            [1] => Peptide
            [2] => Sulfur Compound
            [3] => Sulfonamide
            [4] => Benzenesulfonamide
        )

    [other_name] => Array
        (
            [0] => Tos-Lys-CH2Cl
            [1] => Tosyl-L-lysine chloromethyl ketone
            [2] => TLCK
            [3] => TCK
            [4] => Tosyllysyl chloromethyl ketone
            [5] => N-alpha-p-Tosyl-L-lysine chloromethyl ketone
            [6] => TCK\/PRD_000459
            [7] => N-[(1S)-5-amino-1-(chloroacetyl)pentyl]-4-methylbenzenesulfonamide
            [8] => CHEMBL466465
            [9] => CHEBI:9640
            [10] => SCHEMBL200247
            [11] => ZINC1532775
        )

    [chemical_nomenclature] => N-[(3S)-7-amino-1-chloro-2-oxoheptan-3-yl]-4-methylbenzenesulfonamide
    [formula] => C14H21ClN2O3S
    [cas_number] => 2364-87-6
    [mw] => 332.8
    [pick_me_to_call] => display_script
    [kinetic_parameter] => 
    [paper] => Cengiz_1997_Biochem.Mol.Med_61_52 || Cokugras_2004_Protein.J_23_495 || da Silva-Lopez_2008_Acta.Trop_107_159 || Valkova_2003_J.Biol.Chem_278_12779 || Cowan_2001_J.Appl.Toxicol_21_293 || Timofeev_2021_Crystals_11_1438 || Petrenko_2023_Int.J.Mol.Sci_24_2286
    [comment] => An inhibitor of serine endopeptidases. Acts as an alkylating agent and is known to interfere with the translation process. also inhibits Trypsine
    [gene_locus] => entcl-PRBA || human-BCHE || 9gamm-b3vi58
    [kin_inhibitor] => 
    [cid] => 73094
    [family] => Carb_B_Bacteria || BCHE || S9N_PREPL_Peptidase_S9
    [inchikey] => RDFCSSHDJSZMTQ-ZDUSSCGKSA-N
    [canonicalsmiles] => 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
    [wikipedia] => 
    [iupharlig] => 
    [structure] => 
    [substrate] => 
    [interact_gene_locus] => 
    [mutation] => 
    [comment2] => 
    [extoxnet] => 
    [news] => 
    [theoretical_model] => 
)