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Literature summary for 6.2.1.26 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
Search for more literature for 6.2.1.26

Application

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

Inhibitors

Inhibitors Comment Organism Structure
5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
-
 Escherichia coli
5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
-
 Mycobacterium tuberculosis
5'-([[(1E)-5-(2-carboxyphenyl)-5-oxopent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
-
 Staphylococcus aureus
5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
-
 Escherichia coli
5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
-
 Mycobacterium tuberculosis
5'-([[(1E)-5-(2-carboxyphenyl)pent-1-en-1-yl]sulfonyl]amino)-5'-deoxyadenosine
-
 Staphylococcus aureus
5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine
-
 Escherichia coli
5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine
-
 Mycobacterium tuberculosis
5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine
-
 Staphylococcus aureus
5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine
-
 Escherichia coli
5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine
-
 Mycobacterium tuberculosis
5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine
-
 Staphylococcus aureus
5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine
-
 Escherichia coli
5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine
-
 Mycobacterium tuberculosis
5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]-5-oxopent-1-en-1-yl]sulfonyl)amino]adenosine
-
 Staphylococcus aureus
5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine
-
 Escherichia coli
5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine
-
 Mycobacterium tuberculosis
5'-deoxy-5'-[([(1E)-5-[2-(methoxycarbonyl)phenyl]pent-1-en-1-yl]sulfonyl)amino]adenosine
-
 Staphylococcus aureus
5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine
-
 Escherichia coli
5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine
-
 Mycobacterium tuberculosis
5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine
-
 Staphylococcus aureus
5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine
-
 Escherichia coli
5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine
-
 Mycobacterium tuberculosis
5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine
-
 Staphylococcus aureus
5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine
-
 Escherichia coli
5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine
-
 Mycobacterium tuberculosis
5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine
-
 Staphylococcus aureus
5'-O-([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)adenosine hydrolytically unstable at the acyl sulfamate moiety Escherichia coli
5'-O-([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)adenosine
-
 Mycobacterium tuberculosis
5'-O-([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)adenosine hydrolytically unstable at the acyl sulfamate moiety Staphylococcus aureus
5'-O-[[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]adenosine
-
 Escherichia coli
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
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
5'-O-[[4-(2-carboxyphenyl)butanoyl]sulfamoyl]adenosine
-
 Escherichia coli
5'-O-[[4-(2-carboxyphenyl)butanoyl]sulfamoyl]adenosine
-
 Mycobacterium tuberculosis
5'-O-[[4-(2-carboxyphenyl)butanoyl]sulfamoyl]adenosine
-
 Staphylococcus aureus
additional information structure-function relationship of o-succinylbenzoate-AMP sulfonyladenosine analogue inhibitors, overview Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-
Mycobacterium tuberculosis
-
-
-
Staphylococcus aureus
-
-
-

Reaction

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

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

Synonyms

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

Cofactor

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

Ki Value [mM]

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

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
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
0.0002
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine
0.00024
-
 pH and temperature not specified in the publication Staphylococcus aureus 5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine
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
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
0.00063
-
 pH and temperature not specified in the publication Escherichia coli 5'-([[4-(2-carboxyphenyl)-4-oxobutanoyl]sulfamoyl]amino)-5'-deoxyadenosine
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
0.0142
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine
0.0235
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine
0.0246
-
 pH and temperature not specified in the publication Staphylococcus aureus 5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine
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
0.0341
-
 pH and temperature not specified in the publication Escherichia coli 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine
0.038
-
 pH and temperature not specified in the publication Escherichia coli 5'-O-([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)adenosine
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
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
0.085
-
 pH and temperature not specified in the publication Staphylococcus aureus 5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine
0.101
-
 pH and temperature not specified in the publication Mycobacterium tuberculosis 5'-([[4-(2-carboxyphenyl)butanoyl]sulfamoyl]amino)-5'-deoxyadenosine
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
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
0.2
-
 pH and temperature not specified in the publication Staphylococcus aureus 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]-4-oxobutanoyl]sulfamoyl)amino]adenosine
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
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
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
0.2
-
 pH and temperature not specified in the publication Staphylococcus aureus 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine
0.2
-
 pH and temperature not specified in the publication Escherichia coli 5'-deoxy-5'-[([4-[2-(methoxycarbonyl)phenyl]butanoyl]sulfamoyl)amino]adenosine
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

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