Reaction participants Show >> << Hide
- Name help_outline 2-succinylbenzoate Identifier CHEBI:18325 Charge -2 Formula C11H8O5 InChIKeyhelp_outline YIVWQNVQRXFZJB-UHFFFAOYSA-L SMILEShelp_outline [O-]C(=O)CCC(=O)c1ccccc1C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline ATP Identifier CHEBI:30616 (Beilstein: 3581767) help_outline Charge -4 Formula C10H12N5O13P3 InChIKeyhelp_outline ZKHQWZAMYRWXGA-KQYNXXCUSA-J SMILEShelp_outline Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,284 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline CoA Identifier CHEBI:57287 (Beilstein: 11604429) help_outline Charge -4 Formula C21H32N7O16P3S InChIKeyhelp_outline RGJOEKWQDUBAIZ-IBOSZNHHSA-J SMILEShelp_outline CC(C)(COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP([O-])([O-])=O)n1cnc2c(N)ncnc12)[C@@H](O)C(=O)NCCC(=O)NCCS 2D coordinates Mol file for the small molecule Search links Involved in 1,511 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 2-succinylbenzoyl-CoA Identifier CHEBI:57364 Charge -5 Formula C32H39N7O20P3S InChIKeyhelp_outline KVAQAPQXOXTRAE-HSJNEKGZSA-I SMILEShelp_outline [C@@H]1(N2C3=C(C(=NC=N3)N)N=C2)O[C@H](COP(OP(OCC(C)([C@H](C(NCCC(NCCSC(=O)CCC(=O)C=4C=CC=CC4C(=O)[O-])=O)=O)O)C)(=O)[O-])(=O)[O-])[C@H]([C@H]1O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline AMP Identifier CHEBI:456215 Charge -2 Formula C10H12N5O7P InChIKeyhelp_outline UDMBCSSLTHHNCD-KQYNXXCUSA-L SMILEShelp_outline Nc1ncnc2n(cnc12)[C@@H]1O[C@H](COP([O-])([O-])=O)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 512 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline diphosphate Identifier CHEBI:33019 (Beilstein: 185088) help_outline Charge -3 Formula HO7P2 InChIKeyhelp_outline XPPKVPWEQAFLFU-UHFFFAOYSA-K SMILEShelp_outline OP([O-])(=O)OP([O-])([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 1,139 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:17009 | RHEA:17010 | RHEA:17011 | RHEA:17012 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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4-(2'-Carboxyphenyl)-4-oxobutyryl coenzyme A ester, an intermediate in vitamin K2 (menaquinone) biosynthesis.
Kolkmann R., Leistner E.
Enzyme preparations from Mycobacterium phlei, Escherichia coli and Galium mollugo cell suspension cultures were incubated in the presence of 4-(2'-carboxyphenyl)-4-oxobutyrate (i.e. o-succinylbenzoic acid, OSB, 1), ATP, coenzyme A and Mg2+. The main product isolated from the incubation mixture was ... >> More
Enzyme preparations from Mycobacterium phlei, Escherichia coli and Galium mollugo cell suspension cultures were incubated in the presence of 4-(2'-carboxyphenyl)-4-oxobutyrate (i.e. o-succinylbenzoic acid, OSB, 1), ATP, coenzyme A and Mg2+. The main product isolated from the incubation mixture was 4-(2'-carboxyphenyl)-4-oxobutyryl coenzyme A ester (2) as determined by comparison with synthetic coenzyme A esters. Synthetic and enzymically formed 4-(2'-carboxyphenyl)-4-oxobutyryl coenzyme A ester (2) was shown to be enzymically converted to an intermediate in vitamin K2 biosynthesis viz. 1,4-dihydroxy-2-naphthoic acid (5). The enzymic formation of 2-(3'-Carboxypropionyl)benzoyl coenzyme A ester (3) and 4-(2'-carboxyphenyl)-4-oxobutyryl-di-coenzyme A ester (4) was also observed. They appeared in minor amounts, however. These esters were not convertible to 1,4-dihydroxy-2-naphthoic acid (5). << Less
Z Naturforsch C J Biosci 42:1207-1214(1987) [PubMed] [EuropePMC]
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Menaquinone (vitamin K2) biosynthesis: conversion of o-succinylbenzoic acid to 1,4-dihydroxy-2-naphthoic acid by Mycobacterium phlei enzymes.
Meganathan R., Bentley R.
The coenzyme A (CoA) and adenosine 5'-triphosphate-dependent conversion of o-succinylbenzoic acid (4-[2'-carboxyphenyl]-4-oxobutyric acid) to 1,4-dihydroxy-2-naphthoic acids is an important step in menaquinone (vitamin K2) biosynthesis. Cell-free extracts catalyzing this conversion, obtained from ... >> More
The coenzyme A (CoA) and adenosine 5'-triphosphate-dependent conversion of o-succinylbenzoic acid (4-[2'-carboxyphenyl]-4-oxobutyric acid) to 1,4-dihydroxy-2-naphthoic acids is an important step in menaquinone (vitamin K2) biosynthesis. Cell-free extracts catalyzing this conversion, obtained from Mycobacterium phlei, were separated into three protein fractions by treatment with protamine sulfate. The second fraction (fraction B) and the supernatant (fraction S) alone did not catalyze dihydroxynaphthoate formation, but did so in combination. All of the results were consistent with the formation of an unstable intermediate, likely an o-succinylbenzoyl-CoA compound, by the action of fraction S. Adenosine 5'-triphosphate was required in this reaction and adenosine 5'-monophosphate was formed. This enzyme activity was termed o-succinylbenzoyl-CoA synthetase: the enzyme showed a marked stability to 0.1 N hydrochloric acid. The presumed o-succinylbenzoyl-CoA derivate was rather unstable; under a variety of conditions, it was converted to a spirodilactone form of o-succinylbenzoate. Fraction B contained an enzyme, termed naphthoate synthase, which converted the o-succinylbenzoyl-CoA derivative to 1,4-dihydroxy-2-naphthoate. << Less
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Enzymatic synthesis, characterization, and metabolism of the coenzyme A ester of o-succinylbenzoic acid, an intermediate in menaquinone (vitamin K2) biosynthesis.
Heide L., Arendt S., Leistner E.
The enzymatic synthesis of the "active" o-succinylbenzoic acid is described and the factors controlling its formation are investigated. Tritium-labeled coenzyme A is incorporated into "active" o-succinylbenzoic acid, but label from [2-3H]ATP or [gamma-32P is not, indicating that the active compoun ... >> More
The enzymatic synthesis of the "active" o-succinylbenzoic acid is described and the factors controlling its formation are investigated. Tritium-labeled coenzyme A is incorporated into "active" o-succinylbenzoic acid, but label from [2-3H]ATP or [gamma-32P is not, indicating that the active compound is a coenzyme A thio ester(2). The compound is shown by two different methods to contain 1 mol only of coenzyme A per mol of o-succinylbenzoic acid. The o-succinylbenzoic and coenzyme A ester (2) is unstable at alkaline and neutral pH, but is fairly stable under acid conditions. The coenzyme A ester (2) is converted to 1,4-dihydroxy-2-naphthoic acid (3) by enzyme preparations from Mycobacterium phlei and Escherichia coli without any cofactor requirement. << Less