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Literature summary extracted from

  • Zhulenkovs, D.; Rudevica, Z.; Jaudzems, K.; Turks, M.; Leonchiks, A.
    Discovery and structure-activity relationship studies of irreversible benzisothiazolinone-based inhibitors against Staphylococcus aureus sortase A transpeptidase (2014), Bioorg. Med. Chem., 22, 5988-6003.
    View publication on PubMed

Application

EC Number Application Comment Organism
3.4.22.70 drug development the enzyme is is a promising target for therapies against Gram-positive bacteria, in general, and staphylococci, in particular Staphylococcus aureus

Cloned(Commentary)

EC Number Cloned (Comment) Organism
3.4.22.70 recombinant expression of His6-tagged and of nontagged truncated enzyme mutant variant SrtADELTA59 in Escherichia coli strain BL21(DE3) Staphylococcus aureus

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.4.22.70 1-(3,4-dichlorophenyl)-3-(dimethylamino)propan-1-one
-
 Staphylococcus aureus
3.4.22.70 2-(1-oxoisoindolin-2-yl)acetic acid
-
 Staphylococcus aureus
3.4.22.70 2-(3-oxo-1,2-benzothiazol-2(3H)-yl)-N-(tricyclo[3.3.1.13,7]dec-1-yl)acetamide
-
 Staphylococcus aureus
3.4.22.70 3-(3-oxo-1,2-benzothiazol-2(3H)-yl)propanoic acid
-
 Staphylococcus aureus
3.4.22.70 aminoadamantan
-
 Staphylococcus aureus
3.4.22.70 methyl 1-aminoadamantan-3-carboxylate
-
 Staphylococcus aureus
3.4.22.70 methyl 3-(3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamido)adamantane-1-carboxylate
-
 Staphylococcus aureus
3.4.22.70 methyl 3-(3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamido)adamantane-1-carboxylate
-
 Staphylococcus aureus
3.4.22.70 additional information small molecule library screening, synthesis and analysis of irreversible benzisothiazolinone-based inhibitors of the enzyme, structure-activity relationship, overview. No inhibition by aminoadamantan, methyl 1-aminoadamantan-3-carboxylate, and 2-(1-oxoisoindolin-2-yl)acetic acid. Structure determination of inhibitor 1-SrtA complex using purified recombinant nontagged truncated enzyme mutant variant SrtADELTA59, NMR structure determination and analysis Staphylococcus aureus
3.4.22.70 N'-(2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetyl)adamantane-1-carbohydrazide
-
 Staphylococcus aureus
3.4.22.70 N'-(3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanoyl)adamantane-1-carbohydrazide
-
 Staphylococcus aureus
3.4.22.70 N'-(3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanoyl)adamantane-1-carbohydrazide
-
 Staphylococcus aureus
3.4.22.70 N-(3,5-dimethyladamantan-1-yl)-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide
-
 Staphylococcus aureus
3.4.22.70 N-(3,5-dimethyladamantan-1-yl)-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
3.4.22.70 N-(3,5-dimethyladamantan-1-yl)-3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
3.4.22.70 N-(3-hydroxy-5,7-dimethyladamantan-1-yl)-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide
-
 Staphylococcus aureus
3.4.22.70 N-(3-hydroxy-5,7-dimethyladamantan-1-yl)-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
3.4.22.70 N-(3-hydroxy-5,7-dimethyladamantan-1-yl)-3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
3.4.22.70 N-(3-hydroxyadamantan-1-yl)-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
3.4.22.70 N-(3-ydroxyadamantan-1-yl)-3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
3.4.22.70 N-(adamantan-1-yl)-3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
3.4.22.70 N-adamantan-1-yl-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
3.4.22.70 phenyl vinyl sulfone
-
 Staphylococcus aureus

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
3.4.22.70 cell wall
-
 Staphylococcus aureus 5618
-

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
3.4.22.70 Ca2+ required Staphylococcus aureus

Organism

EC Number Organism UniProt Comment Textmining
3.4.22.70 Staphylococcus aureus
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
3.4.22.70 recombinant nontagged truncated enzyme mutant variant SrtADELTA59 from Escherichia coli strain BL21(DE3) by cation and anion exchange chromatography, dialysis, and gel filtration, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA59 from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and gel filtration Staphylococcus aureus

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.4.22.70 Dabcyl-QALPETGEE-Edans + H2O
-
 Staphylococcus aureus Dabcyl-QALPET + GEE-Edans
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.4.22.70 sortase A transpeptidase
-
 Staphylococcus aureus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.4.22.70 37
-
 assay at Staphylococcus aureus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.4.22.70 7.5
-
 assay at Staphylococcus aureus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.4.22.70 0.00339
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA74 Staphylococcus aureus N'-(3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanoyl)adamantane-1-carbohydrazide
3.4.22.70 0.0038
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA72 Staphylococcus aureus N'-(2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetyl)adamantane-1-carbohydrazide
3.4.22.70 0.00381
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA62 Staphylococcus aureus N-adamantan-1-yl-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
3.4.22.70 0.00387
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA61 Staphylococcus aureus N-(3-hydroxy-5,7-dimethyladamantan-1-yl)-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide
3.4.22.70 0.00396
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA69 Staphylococcus aureus N-(3-hydroxy-5,7-dimethyladamantan-1-yl)-3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
3.4.22.70 0.00401
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA67 Staphylococcus aureus N-(adamantan-1-yl)-3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
3.4.22.70 0.0041
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA68 Staphylococcus aureus N-(3,5-dimethyladamantan-1-yl)-3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
3.4.22.70 0.00422
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA73 Staphylococcus aureus N'-(3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanoyl)adamantane-1-carbohydrazide
3.4.22.70 0.00462
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA63 Staphylococcus aureus N-(3,5-dimethyladamantan-1-yl)-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
3.4.22.70 0.00499
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA60 Staphylococcus aureus N-(3,5-dimethyladamantan-1-yl)-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide
3.4.22.70 0.00506
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA71 Staphylococcus aureus methyl 3-(3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamido)adamantane-1-carboxylate
3.4.22.70 0.00508
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA66 Staphylococcus aureus methyl 3-(3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamido)adamantane-1-carboxylate
3.4.22.70 0.00611
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA59 Staphylococcus aureus 2-(3-oxo-1,2-benzothiazol-2(3H)-yl)-N-(tricyclo[3.3.1.13,7]dec-1-yl)acetamide
3.4.22.70 0.00626
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA70 Staphylococcus aureus N-(3-ydroxyadamantan-1-yl)-3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
3.4.22.70 0.00644
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA65 Staphylococcus aureus N-(3-hydroxyadamantan-1-yl)-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
3.4.22.70 0.00706
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA64 Staphylococcus aureus N-(3-hydroxy-5,7-dimethyladamantan-1-yl)-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
3.4.22.70 0.0128
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA75 Staphylococcus aureus 3-(3-oxo-1,2-benzothiazol-2(3H)-yl)propanoic acid
3.4.22.70 0.0169
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA75 Staphylococcus aureus phenyl vinyl sulfone
3.4.22.70 0.736
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA75 Staphylococcus aureus 1-(3,4-dichlorophenyl)-3-(dimethylamino)propan-1-one

General Information

EC Number General Information Comment Organism
3.4.22.70 physiological function as a transpeptidase that covalently attaches various virulence factors to the cell surface, this enzyme plays a crucial role in the ability of bacteria to invade the host's tissues and to escape the immune response Staphylococcus aureus