Reaction participants Show >> << Hide
- Name help_outline (8S)-8-amino-7-oxononanoate Identifier CHEBI:149468 Charge 0 Formula C9H17NO3 InChIKeyhelp_outline GUAHPAJOXVYFON-ZETCQYMHSA-N SMILEShelp_outline C(CCCCCC([C@H](C)[NH3+])=O)(=O)[O-] 2D coordinates Mol file for the small molecule Search links Involved in 7 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
L-lysyl-[protein]
Identifier
RHEA-COMP:9752
Reactive part
help_outline
- Name help_outline L-lysine residue Identifier CHEBI:29969 Charge 1 Formula C6H13N2O SMILEShelp_outline C([C@@H](C(*)=O)N*)CCC[NH3+] 2D coordinates Mol file for the small molecule Search links Involved in 137 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline CO2 Identifier CHEBI:16526 (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 1,006 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
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Namehelp_outline
(S)-2-amino-6-oxohexanoyl-[protein]
Identifier
RHEA-COMP:12448
Reactive part
help_outline
- Name help_outline (S)-2-amino-6-oxohexanoate residue Identifier CHEBI:131803 Charge 0 Formula C6H9NO2 SMILEShelp_outline [H]C(CCC[C@@H](C(*)=O)N*)=O 2D coordinates Mol file for the small molecule Search links Involved in 5 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (7R,8S)-8-amino-7-(carboxyamino)nonanoate Identifier CHEBI:149470 Charge -1 Formula C10H19N2O4 InChIKeyhelp_outline OQNJZSIPDMTUAJ-JGVFFNPUSA-M SMILEShelp_outline C(CCCCC[C@H]([C@H](C)[NH3+])NC(=O)[O-])(=O)[O-] 2D coordinates Mol file for the small molecule Search links Involved in 5 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 9,521 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:63660 | RHEA:63661 | RHEA:63662 | RHEA:63663 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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A suicide enzyme catalyzes multiple reactions for biotin biosynthesis in cyanobacteria.
Sakaki K., Ohishi K., Shimizu T., Kobayashi I., Mori N., Matsuda K., Tomita T., Watanabe H., Tanaka K., Kuzuyama T., Nishiyama M.
In biotin biosynthesis, the conversion of pimeloyl intermediates to biotin is catalyzed by a universal set of four enzymes: BioF, BioA, BioD and BioB. We found that the gene homologous to bioA, the product of which is involved in the conversion of 8-amino-7-oxononanoate (AON) to 7,8-diaminononanoa ... >> More
In biotin biosynthesis, the conversion of pimeloyl intermediates to biotin is catalyzed by a universal set of four enzymes: BioF, BioA, BioD and BioB. We found that the gene homologous to bioA, the product of which is involved in the conversion of 8-amino-7-oxononanoate (AON) to 7,8-diaminononanoate (DAN), is missing in the genome of the cyanobacterium Synechocystis sp. PCC 6803. We provide structural and biochemical evidence showing that a novel dehydrogenase, BioU, is involved in biotin biosynthesis and functionally replaces BioA. This enzyme catalyzes three reactions: formation of covalent linkage with AON to yield a BioU-DAN conjugate at the ε-amino group of Lys124 of BioU using NAD(P)H, carboxylation of the conjugate to form BioU-DAN-carbamic acid, and release of DAN-carbamic acid using NAD(P)<sup>+</sup>. In this biosynthetic pathway, BioU is a suicide enzyme that loses the Lys124 amino group after a single round of reaction. << Less
Nat. Chem. Biol. 16:415-422(2020) [PubMed] [EuropePMC]
This publication is cited by 6 other entries.
Comments
Multi-step reaction: RHEA:63664 and RHEA:63668. Multi-step reaction: RHEA:63672 and RHEA:63676.