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

BRENDA support

Literature summary for 3.4.22.70 extracted from

  • Kudryavtsev, K.V.; Bentley, M.L.; McCafferty, D.G.
    Probing of the cis-5-phenyl proline scaffold as a platform for the synthesis of mechanism-based inhibitors of the Staphylococcus aureus sortase SrtA isoform (2009), Bioorg. Med. Chem., 17, 2886-2893.
    View publication on PubMedView publication on EuropePMC
Search for more literature for 3.4.22.70

Application

Application Comment Organism
medicine 4-vinylsulfonyl 5-phenyl prolinates inhibit Staphylococcus aureus sortase SrtA irreversibly by modification of the enzyme Cys184 and could be used as hits for the development of antibacterials and antivirulence agents Staphylococcus aureus

Cloned(Commentary)

Cloned (Comment) Organism
N-terminally His6-tagged SrtA lacking the amino-terminal 24 amino acids is expressed in BL21(DE3) cells containing the plasmid pET15bSrtADN24 Staphylococcus aureus

Inhibitors

Inhibitors Comment Organism Structure
methyl (2S,3S,7aS)-2-ethenesulfonyl-5-oxo-3-phenyltetrahydropyrrolizine-7a-carboxylate
-
 Staphylococcus aureus
methyl (2S,3S,7aS)-2-ethenesulfonyl-5-oxo-3-pyridin-3-yl-tetrahydropyrrolizine-7a-carboxylate
-
 Staphylococcus aureus
methyl (2S,3S,7aS)-3-(3,4-dimethoxyphenyl)-2-ethenesulfonyl-5-oxotetrahydropyrrolizine-7a-carboxylate
-
 Staphylococcus aureus
methyl (2S,4S,5S)-4-ethenesulfonyl-2-(2-methoxycarbonylethyl)-5-pyridin-3-yl-pyrrolidine-2-carboxylate
-
 Staphylococcus aureus
methyl (4S,5S)-4-(ethenylsulfonyl)-5-(2-fluorophenyl)-L-prolinate
-
 Staphylococcus aureus
methyl (4S,5S)-4-(ethenylsulfonyl)-5-(3-fluorophenyl)-L-prolinate
-
 Staphylococcus aureus
methyl (4S,5S)-4-(ethenylsulfonyl)-5-phenyl-L-prolinate
-
 Staphylococcus aureus

Organism

Organism UniProt Comment Textmining
Staphylococcus aureus
-
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant SrtA lacking the amino-terminal 24 amino acids Staphylococcus aureus

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
Abz-LPETG-Dap(Dnp)-NH2 + Gly5 transpeptidation of LPXTG-containing peptides to the cell-wall precursor mimic NH2-Ala2 Staphylococcus aureus ?
-
 ?

Synonyms

Synonyms Comment Organism
sortase SrtA
-
 Staphylococcus aureus

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.85
-
 pH 7.5, 37°C Staphylococcus aureus methyl (4S,5S)-4-(ethenylsulfonyl)-5-phenyl-L-prolinate
1.04
-
 pH 7.5, 37°C Staphylococcus aureus methyl (4S,5S)-4-(ethenylsulfonyl)-5-(3-fluorophenyl)-L-prolinate
1.32
-
 pH 7.5, 37°C Staphylococcus aureus methyl (4S,5S)-4-(ethenylsulfonyl)-5-(2-fluorophenyl)-L-prolinate
1.86
-
 pH 7.5, 37°C Staphylococcus aureus methyl (2S,4S,5S)-4-ethenesulfonyl-2-(2-methoxycarbonylethyl)-5-pyridin-3-yl-pyrrolidine-2-carboxylate
2.2
-
 pH 7.5, 37°C Staphylococcus aureus methyl (2S,3S,7aS)-2-ethenesulfonyl-5-oxo-3-phenyltetrahydropyrrolizine-7a-carboxylate
2.47
-
 pH 7.5, 37°C Staphylococcus aureus methyl (2S,3S,7aS)-2-ethenesulfonyl-5-oxo-3-pyridin-3-yl-tetrahydropyrrolizine-7a-carboxylate
2.68
-
 pH 7.5, 37°C Staphylococcus aureus methyl (2S,3S,7aS)-3-(3,4-dimethoxyphenyl)-2-ethenesulfonyl-5-oxotetrahydropyrrolizine-7a-carboxylate