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Literature summary extracted from

  • Lu, X.; Zhou, R.; Sharma, I.; Li, X.; Kumar, G.; Swaminathan, S.; Tonge, P.J.; Tan, D.S.
    Stable analogues of OSB-AMP: potent inhibitors of MenE, the o-succinylbenzoate-CoA synthetase from bacterial menaquinone biosynthesis (2012), ChemBioChem, 13, 129-136.
    View publication on PubMedView publication on EuropePMC

Application

EC Number Application Comment Organism
6.2.1.26 drug development the enzyme is an attractive target for blocking menaquinone biosynthesis as an antibacterial strategy Escherichia coli
6.2.1.26 drug development the enzyme is an attractive target for blocking menaquinone biosynthesis as an antibacterial strategy Mycobacterium tuberculosis

Inhibitors

EC Number Inhibitors Comment Organism Structure
6.2.1.26 5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
-
 Escherichia coli
6.2.1.26 5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
-
 Mycobacterium tuberculosis
6.2.1.26 5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
-
 Staphylococcus aureus
6.2.1.26 5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
-
 Escherichia coli
6.2.1.26 5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
-
 Mycobacterium tuberculosis
6.2.1.26 5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
-
 Staphylococcus aureus
6.2.1.26 5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine
-
 Escherichia coli
6.2.1.26 5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine
-
 Mycobacterium tuberculosis
6.2.1.26 5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine
-
 Staphylococcus aureus
6.2.1.26 5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine
-
 Escherichia coli
6.2.1.26 5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine
-
 Mycobacterium tuberculosis
6.2.1.26 5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine
-
 Staphylococcus aureus
6.2.1.26 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine
-
 Escherichia coli
6.2.1.26 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine
-
 Mycobacterium tuberculosis
6.2.1.26 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine
-
 Staphylococcus aureus
6.2.1.26 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine
-
 Escherichia coli
6.2.1.26 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine
-
 Mycobacterium tuberculosis
6.2.1.26 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine
-
 Staphylococcus aureus
6.2.1.26 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine
-
 Escherichia coli
6.2.1.26 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine
-
 Mycobacterium tuberculosis
6.2.1.26 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine
-
 Staphylococcus aureus
6.2.1.26 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine
-
 Escherichia coli
6.2.1.26 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine
-
 Mycobacterium tuberculosis
6.2.1.26 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine
-
 Staphylococcus aureus
6.2.1.26 5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine
-
 Escherichia coli
6.2.1.26 5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine
-
 Mycobacterium tuberculosis
6.2.1.26 5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine
-
 Staphylococcus aureus
6.2.1.26 5'-O-([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)adenosine hydrolytically unstable at the acyl sulfamate moiety Escherichia coli
6.2.1.26 5'-O-([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)adenosine
-
 Mycobacterium tuberculosis
6.2.1.26 5'-O-([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)adenosine hydrolytically unstable at the acyl sulfamate moiety Staphylococcus aureus
6.2.1.26 5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine
-
 Escherichia coli
6.2.1.26 5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine sulfonyladenosine analogue of the cognate reaction intermediate, o-succinylbenzoate-AMP, competitive inhibitor of mtMenE with respect to ATP and a noncompetitive inhibitor with respect to 2-succinylbenzoate Mycobacterium tuberculosis
6.2.1.26 5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine sulfonyladenosine analogue of the cognate reaction intermediate, o-succinylbenzoate-AMP. Putative active site residues, Arg222 and Ser302, may interact with the 2-succinylbenzoate aromatic carboxylate and bind the 2-succinylbenzoate ketone oxygen, respectively, computational docking of 2-succinylbenzoate-AMP with the unliganded crystal structure of saMenE Staphylococcus aureus
6.2.1.26 5'-O-[[4-(2-carboxyphenyl)butanoyl]sulfamoyl]adenosine
-
 Escherichia coli
6.2.1.26 5'-O-[[4-(2-carboxyphenyl)butanoyl]sulfamoyl]adenosine
-
 Mycobacterium tuberculosis
6.2.1.26 5'-O-[[4-(2-carboxyphenyl)butanoyl]sulfamoyl]adenosine
-
 Staphylococcus aureus
6.2.1.26 additional information structure-function relationship of o-succinylbenzoate-AMP sulfonyladenosine analogue inhibitors, overview Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
6.2.1.26 ATP + 2-succinylbenzoate + CoA Staphylococcus aureus
-
 AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA
-
 ?
6.2.1.26 ATP + 2-succinylbenzoate + CoA Escherichia coli
-
 AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA
-
 ?
6.2.1.26 ATP + 2-succinylbenzoate + CoA Mycobacterium tuberculosis
-
 AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
6.2.1.26 Escherichia coli
-
-
-
6.2.1.26 Mycobacterium tuberculosis
-
-
-
6.2.1.26 Staphylococcus aureus
-
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
6.2.1.26 ATP + 2-succinylbenzoate + CoA = AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA bi uni uni bi ping-pong kinetic mechanism Staphylococcus aureus
a
6.2.1.26 ATP + 2-succinylbenzoate + CoA = AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA bi uni uni bi ping-pong kinetic mechanism Escherichia coli
a
6.2.1.26 ATP + 2-succinylbenzoate + CoA = AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA bi uni uni bi ping-pong kinetic mechanism Mycobacterium tuberculosis
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
6.2.1.26 ATP + 2-succinylbenzoate + CoA
-
 Staphylococcus aureus AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA
-
 ?
6.2.1.26 ATP + 2-succinylbenzoate + CoA
-
 Escherichia coli AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA
-
 ?
6.2.1.26 ATP + 2-succinylbenzoate + CoA
-
 Mycobacterium tuberculosis AMP + diphosphate + 4-(2-carboxyphenyl)-4-oxobutanoyl-CoA
-
 ?

Synonyms

EC Number Synonyms Comment Organism
6.2.1.26 MenE
-
 Staphylococcus aureus
6.2.1.26 MenE
-
 Escherichia coli
6.2.1.26 MenE
-
 Mycobacterium tuberculosis
6.2.1.26 o-succinylbenzoate-CoA synthetase
-
 Staphylococcus aureus
6.2.1.26 o-succinylbenzoate-CoA synthetase
-
 Escherichia coli
6.2.1.26 o-succinylbenzoate-CoA synthetase
-
 Mycobacterium tuberculosis
6.2.1.26 OSB-CoA synthetase
-
 Staphylococcus aureus
6.2.1.26 OSB-CoA synthetase
-
 Escherichia coli
6.2.1.26 OSB-CoA synthetase
-
 Mycobacterium tuberculosis

Cofactor

EC Number Cofactor Comment Organism Structure
6.2.1.26 ATP
-
 Staphylococcus aureus
6.2.1.26 ATP
-
 Escherichia coli
6.2.1.26 ATP
-
 Mycobacterium tuberculosis

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
6.2.1.26 0.0054
-
 5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine versus ATP, pH and temperature not specified in the publication Mycobacterium tuberculosis
6.2.1.26 0.0112
-
 5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine versus 2-succinylbenzoate, pH and temperature not specified in the publication Mycobacterium tuberculosis
6.2.1.26 0.022
-
 5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine pH and temperature not specified in the publication Staphylococcus aureus
6.2.1.26 0.128
-
 5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine pH and temperature not specified in the publication Escherichia coli

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
6.2.1.26 0.00016
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
6.2.1.26 0.0002
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine
6.2.1.26 0.00024
-
 pH and temperature not specified in the publication Staphylococcus aureus 5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine
6.2.1.26 0.00033
-
 pH and temperature not specified in the publication Staphylococcus aureus 5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
6.2.1.26 0.00057
-
 pH and temperature not specified in the publication Escherichia coli 5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
6.2.1.26 0.00063
-
 pH and temperature not specified in the publication Escherichia coli 5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine
6.2.1.26 0.0057
-
 pH and temperature not specified in the publication Escherichia coli 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine
6.2.1.26 0.0142
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine
6.2.1.26 0.0235
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine
6.2.1.26 0.0246
-
 pH and temperature not specified in the publication Staphylococcus aureus 5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine
6.2.1.26 0.0316
-
 pH and temperature not specified in the publication Escherichia coli 5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
6.2.1.26 0.0341
-
 pH and temperature not specified in the publication Escherichia coli 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine
6.2.1.26 0.038
-
 pH and temperature not specified in the publication Escherichia coli 5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine
6.2.1.26 0.0457
-
 pH and temperature not specified in the publication Staphylococcus aureus 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine
6.2.1.26 0.0544
-
 pH and temperature not specified in the publication Staphylococcus aureus 5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
6.2.1.26 0.085
-
 pH and temperature not specified in the publication Staphylococcus aureus 5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine
6.2.1.26 0.101
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine
6.2.1.26 0.106
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
6.2.1.26 0.117
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine
6.2.1.26 0.2
-
 pH and temperature not specified in the publication Staphylococcus aureus 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine
6.2.1.26 0.2
-
 pH and temperature not specified in the publication Staphylococcus aureus 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine
6.2.1.26 0.2
-
 pH and temperature not specified in the publication Escherichia coli 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine
6.2.1.26 0.2
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine
6.2.1.26 0.2
-
 pH and temperature not specified in the publication Staphylococcus aureus 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine
6.2.1.26 0.2
-
 pH and temperature not specified in the publication Escherichia coli 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine
6.2.1.26 0.2
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine

General Information

EC Number General Information Comment Organism
6.2.1.26 additional information the basic residue, Arg222, may interact with the aromatic carboxylate of 2-succinylbenzoate Staphylococcus aureus
6.2.1.26 additional information the basic residue, Arg222, may interact with the aromatic carboxylate of 2-succinylbenzoate Escherichia coli
6.2.1.26 additional information the basic residue, Arg222, may interact with the aromatic carboxylate of 2-succinylbenzoate Mycobacterium tuberculosis
6.2.1.26 physiological function the enzyme is essential in Escherichia coli and is involved in menaquinone biosynthesis Escherichia coli
6.2.1.26 physiological function the enzyme is essential in Mycobacterium tuberculosis and is involved in menaquinone biosynthesis Mycobacterium tuberculosis
6.2.1.26 physiological function the enzyme is important in Mycobacterium tuberculosis Staphylococcus aureus