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Literature summary 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

Application

EC Number Application Comment Organism
3.4.22.70 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)

EC Number Cloned (Comment) Organism
3.4.22.70 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

EC Number Inhibitors Comment Organism Structure
3.4.22.70 methyl (2S,3S,7aS)-2-ethenesulfonyl-5-oxo-3-phenyltetrahydropyrrolizine-7a-carboxylate
-
 Staphylococcus aureus
3.4.22.70 methyl (2S,3S,7aS)-2-ethenesulfonyl-5-oxo-3-pyridin-3-yl-tetrahydropyrrolizine-7a-carboxylate
-
 Staphylococcus aureus
3.4.22.70 methyl (2S,3S,7aS)-3-(3,4-dimethoxyphenyl)-2-ethenesulfonyl-5-oxotetrahydropyrrolizine-7a-carboxylate
-
 Staphylococcus aureus
3.4.22.70 methyl (2S,4S,5S)-4-ethenesulfonyl-2-(2-methoxycarbonylethyl)-5-pyridin-3-yl-pyrrolidine-2-carboxylate
-
 Staphylococcus aureus
3.4.22.70 methyl (4S,5S)-4-(ethenylsulfonyl)-5-(2-fluorophenyl)-L-prolinate
-
 Staphylococcus aureus
3.4.22.70 methyl (4S,5S)-4-(ethenylsulfonyl)-5-(3-fluorophenyl)-L-prolinate
-
 Staphylococcus aureus
3.4.22.70 methyl (4S,5S)-4-(ethenylsulfonyl)-5-phenyl-L-prolinate
-
 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 SrtA lacking the amino-terminal 24 amino acids Staphylococcus aureus

Substrates and Products (Substrate)

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

Synonyms

EC Number Synonyms Comment Organism
3.4.22.70 sortase SrtA
-
 Staphylococcus aureus

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.4.22.70 0.85
-
 pH 7.5, 37°C Staphylococcus aureus methyl (4S,5S)-4-(ethenylsulfonyl)-5-phenyl-L-prolinate
3.4.22.70 1.04
-
 pH 7.5, 37°C Staphylococcus aureus methyl (4S,5S)-4-(ethenylsulfonyl)-5-(3-fluorophenyl)-L-prolinate
3.4.22.70 1.32
-
 pH 7.5, 37°C Staphylococcus aureus methyl (4S,5S)-4-(ethenylsulfonyl)-5-(2-fluorophenyl)-L-prolinate
3.4.22.70 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
3.4.22.70 2.2
-
 pH 7.5, 37°C Staphylococcus aureus methyl (2S,3S,7aS)-2-ethenesulfonyl-5-oxo-3-phenyltetrahydropyrrolizine-7a-carboxylate
3.4.22.70 2.47
-
 pH 7.5, 37°C Staphylococcus aureus methyl (2S,3S,7aS)-2-ethenesulfonyl-5-oxo-3-pyridin-3-yl-tetrahydropyrrolizine-7a-carboxylate
3.4.22.70 2.68
-
 pH 7.5, 37°C Staphylococcus aureus methyl (2S,3S,7aS)-3-(3,4-dimethoxyphenyl)-2-ethenesulfonyl-5-oxotetrahydropyrrolizine-7a-carboxylate