Reaction participants Show >> << Hide
- Name help_outline (indol-3-yl)acetyl-AMP Identifier CHEBI:188353 Charge -1 Formula C20H20N6O8P InChIKeyhelp_outline BCGXTVVDYBAZGZ-AEVYOOLXSA-M SMILEShelp_outline C1=CC=CC=2NC=C(C12)CC(OP(OC[C@H]3O[C@@H](N4C=5N=CN=C(N)C5N=C4)[C@@H]([C@@H]3O)O)(=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 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 1,567 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (indol-3-yl)acetyl-CoA Identifier CHEBI:57271 Charge -4 Formula C31H39N8O17P3S InChIKeyhelp_outline WXOGUAPLOCTRFO-HSJNEKGZSA-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)NCCSC(=O)Cc1c[nH]c2ccccc12 2D coordinates Mol file for the small molecule Search links Involved in 4 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 529 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,932 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:69723 | RHEA:69724 | RHEA:69725 | RHEA:69726 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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An indoleacetate-CoA ligase and a phenylsuccinyl-CoA transferase involved in anaerobic metabolism of auxin.
Schuehle K., Nies J., Heider J.
The plant hormone auxin (indoleacetate) is anaerobically degraded by the Betaproteobacterium Aromatoleum aromaticum. We report here on a CoA ligase (IaaB) and a CoA-transferase (IaaL) which are encoded in the apparent substrate-induced iaa operon containing genes for indoleacetate degradation. Iaa ... >> More
The plant hormone auxin (indoleacetate) is anaerobically degraded by the Betaproteobacterium Aromatoleum aromaticum. We report here on a CoA ligase (IaaB) and a CoA-transferase (IaaL) which are encoded in the apparent substrate-induced iaa operon containing genes for indoleacetate degradation. IaaB is a highly specific indoleacetate-CoA ligase which activates indoleacetate to the CoA-thioester immediately after uptake into the cytoplasm. This enzyme only activates indoleacetate and some closely related compounds such as naphthylacetate, phenylacetate and indolepropionate, and is inhibited by high concentrations of substrates, and by the synthetic auxin compound 2,4-dichlorophenoxyacetate, which does not serve as substrate. IaaL is a CoA-transferase recognizing several C4-dicarboxylic acids, such as succinate, phenylsuccinate or benzylsuccinate and their CoA-thioesters, but only few monocarboxylic acids and no C3-dicarboxylic acids such as benzylmalonate. The enzyme shows no stereospecific discrimation of the benzylsuccinate enantiomers. Moreover, benzylsuccinate is regiospecifically activated to 2-benzylsuccinyl-CoA, whereas phenylsuccinate is converted to an equal mixture of both regioisomers (2- and 3-phenylsuccinyl-CoA). The identification of these two enzymes allows us to set up a modified version of the metabolic pathway of anaerobic indoleacetate degradation and to investigate the sequences databases for the occurrence and distribution of this pathway in other microorgansisms. << Less
Environ. Microbiol. 18:3120-3132(2016) [PubMed] [EuropePMC]
This publication is cited by 13 other entries.
Comments
RHEA:69723 part of RHEA:69715