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- Name help_outline (E)-2-((N-methylformamido) methylene)succinate Identifier CHEBI:141414 Charge -2 Formula C7H7NO5 InChIKeyhelp_outline KAJVKDPSEUVDTF-HWKANZROSA-L SMILEShelp_outline C(/C(/C([O-])=O)=C\N(C)C=O)C(=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 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 9,431 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H2O Identifier CHEBI:15377 (Beilstein: 3587155; CAS: 7732-18-5) help_outline Charge 0 Formula H2O InChIKeyhelp_outline XLYOFNOQVPJJNP-UHFFFAOYSA-N SMILEShelp_outline [H]O[H] 2D coordinates Mol file for the small molecule Search links Involved in 6,204 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline CO2 Identifier CHEBI:16526 (Beilstein: 1900390; CAS: 124-38-9) help_outline Charge 0 Formula CO2 InChIKeyhelp_outline CURLTUGMZLYLDI-UHFFFAOYSA-N SMILEShelp_outline O=C=O 2D coordinates Mol file for the small molecule Search links Involved in 997 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline formate Identifier CHEBI:15740 (Beilstein: 1901205; CAS: 71-47-6) help_outline Charge -1 Formula CHO2 InChIKeyhelp_outline BDAGIHXWWSANSR-UHFFFAOYSA-M SMILEShelp_outline [H]C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 97 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline methylamine Identifier CHEBI:59338 Charge 1 Formula CH6N InChIKeyhelp_outline BAVYZALUXZFZLV-UHFFFAOYSA-O SMILEShelp_outline C[NH3+] 2D coordinates Mol file for the small molecule Search links Involved in 27 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline succinate semialdehyde Identifier CHEBI:57706 Charge -1 Formula C4H5O3 InChIKeyhelp_outline UIUJIQZEACWQSV-UHFFFAOYSA-M SMILEShelp_outline [O-]C(=O)CCC=O 2D coordinates Mol file for the small molecule Search links Involved in 17 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:57032 | RHEA:57033 | RHEA:57034 | RHEA:57035 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Elucidation of the trigonelline degradation pathway reveals previously undescribed enzymes and metabolites.
Perchat N., Saaidi P.L., Darii E., Pelle C., Petit J.L., Besnard-Gonnet M., de Berardinis V., Dupont M., Gimbernat A., Salanoubat M., Fischer C., Perret A.
Trigonelline (TG; <i>N-</i>methylnicotinate) is a ubiquitous osmolyte. Although it is known that it can be degraded, the enzymes and metabolites have not been described so far. In this work, we challenged the laboratory model soil-borne, gram-negative bacterium <i>Acinetobacter baylyi</i> ADP1 (AD ... >> More
Trigonelline (TG; <i>N-</i>methylnicotinate) is a ubiquitous osmolyte. Although it is known that it can be degraded, the enzymes and metabolites have not been described so far. In this work, we challenged the laboratory model soil-borne, gram-negative bacterium <i>Acinetobacter baylyi</i> ADP1 (ADP1) for its ability to grow on TG and we identified a cluster of catabolic, transporter, and regulatory genes. We dissected the pathway to the level of enzymes and metabolites, and proceeded to in vitro reconstruction of the complete pathway by six purified proteins. The four enzymatic steps that lead from TG to methylamine and succinate are described, and the structures of previously undescribed metabolites are provided. Unlike many aromatic compounds that undergo hydroxylation prior to ring cleavage, the first step of TG catabolism proceeds through direct cleavage of the C5-C6 bound, catalyzed by a flavin-dependent, two-component oxygenase, which yields (<i>Z</i>)-2-((<i>N-</i>methylformamido)methylene)-5-hydroxy-butyrolactone (MFMB). MFMB is then oxidized into (<i>E</i>)-2-((<i>N-</i>methylformamido) methylene) succinate (MFMS), which is split up by a hydrolase into carbon dioxide, methylamine, formic acid, and succinate semialdehyde (SSA). SSA eventually fuels up the TCA by means of an SSA dehydrogenase, assisted by a Conserved Hypothetical Protein. The cluster is conserved across marine, soil, and plant-associated bacteria. This emphasizes the role of TG as a ubiquitous nutrient for which an efficient microbial catabolic toolbox is available. << Less
Proc. Natl. Acad. Sci. U.S.A. 115:E4358-E4367(2018) [PubMed] [EuropePMC]
This publication is cited by 4 other entries.