Any feedback?
Please rate this page
(literature.php)
(0/150)

BRENDA support

Literature summary for 3.4.22.70 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
Search for more literature for 3.4.22.70

Application

Application Comment Organism
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)

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

Inhibitors

Inhibitors Comment Organism Structure
1-(3,4-dichlorophenyl)-3-(dimethylamino)propan-1-one
-
 Staphylococcus aureus
2-(1-oxoisoindolin-2-yl)acetic acid
-
 Staphylococcus aureus
2-(3-oxo-1,2-benzothiazol-2(3H)-yl)-N-(tricyclo[3.3.1.13,7]dec-1-yl)acetamide
-
 Staphylococcus aureus
3-(3-oxo-1,2-benzothiazol-2(3H)-yl)propanoic acid
-
 Staphylococcus aureus
aminoadamantan
-
 Staphylococcus aureus
methyl 1-aminoadamantan-3-carboxylate
-
 Staphylococcus aureus
methyl 3-(3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamido)adamantane-1-carboxylate
-
 Staphylococcus aureus
methyl 3-(3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamido)adamantane-1-carboxylate
-
 Staphylococcus aureus
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
N'-(2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetyl)adamantane-1-carbohydrazide
-
 Staphylococcus aureus
N'-(3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanoyl)adamantane-1-carbohydrazide
-
 Staphylococcus aureus
N'-(3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanoyl)adamantane-1-carbohydrazide
-
 Staphylococcus aureus
N-(3,5-dimethyladamantan-1-yl)-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide
-
 Staphylococcus aureus
N-(3,5-dimethyladamantan-1-yl)-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
N-(3,5-dimethyladamantan-1-yl)-3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
N-(3-hydroxy-5,7-dimethyladamantan-1-yl)-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide
-
 Staphylococcus aureus
N-(3-hydroxy-5,7-dimethyladamantan-1-yl)-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
N-(3-hydroxy-5,7-dimethyladamantan-1-yl)-3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
N-(3-hydroxyadamantan-1-yl)-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
N-(3-ydroxyadamantan-1-yl)-3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
N-(adamantan-1-yl)-3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
N-adamantan-1-yl-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide
-
 Staphylococcus aureus
phenyl vinyl sulfone
-
 Staphylococcus aureus

Localization

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

Metals/Ions

Metals/Ions Comment Organism Structure
Ca2+ required Staphylococcus aureus

Organism

Organism UniProt Comment Textmining
Staphylococcus aureus
-
-
-

Purification (Commentary)

Purification (Comment) Organism
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)

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

Synonyms

Synonyms Comment Organism
sortase A transpeptidase
-
 Staphylococcus aureus

Temperature Optimum [°C]

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

pH Optimum

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

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
0.0169
-
 pH 7.5, 37°C, recombinant His6-tagged truncated enzyme mutant variant SrtADELTA75 Staphylococcus aureus phenyl vinyl sulfone
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

General Information Comment Organism
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