Enzymes
| UniProtKB help_outline | 1 proteins |
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- Name help_outline 2-hydroxyisobutanoyl-CoA Identifier CHEBI:131780 Charge -4 Formula C25H38N7O18P3S InChIKeyhelp_outline FFVUICCDNWZCRC-ZSJPKINUSA-J 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)C(C)(C)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 3 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline formyl-CoA Identifier CHEBI:57376 Charge -4 Formula C22H32N7O17P3S InChIKeyhelp_outline SXMOKYXNAPLNCW-GORZOVPNSA-J SMILEShelp_outline [H]C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(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 2D coordinates Mol file for the small molecule Search links Involved in 12 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline acetone Identifier CHEBI:15347 (CAS: 67-64-1) help_outline Charge 0 Formula C3H6O InChIKeyhelp_outline CSCPPACGZOOCGX-UHFFFAOYSA-N SMILEShelp_outline CC(C)=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:69424 | RHEA:69425 | RHEA:69426 | RHEA:69427 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Actinobacterial Degradation of 2-Hydroxyisobutyric Acid Proceeds via Acetone and Formyl-CoA by Employing a Thiamine-Dependent Lyase Reaction.
Rohwerder T., Rohde M.T., Jehmlich N., Purswani J.
The tertiary branched short-chain 2-hydroxyisobutyric acid (2-HIBA) has been associated with several metabolic diseases and lysine 2-hydroxyisobutyrylation seems to be a common eukaryotic as well as prokaryotic post-translational modification in proteins. In contrast, the underlying 2-HIBA metabol ... >> More
The tertiary branched short-chain 2-hydroxyisobutyric acid (2-HIBA) has been associated with several metabolic diseases and lysine 2-hydroxyisobutyrylation seems to be a common eukaryotic as well as prokaryotic post-translational modification in proteins. In contrast, the underlying 2-HIBA metabolism has thus far only been detected in a few microorganisms, such as the betaproteobacterium <i>Aquincola tertiaricarbonis</i> L108 and the <i>Bacillus</i> group bacterium <i>Kyrpidia tusciae</i> DSM 2912. In these strains, 2-HIBA can be specifically activated to the corresponding CoA thioester by the 2-HIBA-CoA ligase (HCL) and is then isomerized to 3-hydroxybutyryl-CoA in a reversible and B<sub>12</sub>-dependent mutase reaction. Here, we demonstrate that the actinobacterial strain <i>Actinomycetospora chiangmaiensis</i> DSM 45062 degrades 2-HIBA and also its precursor 2-methylpropane-1,2-diol via acetone and formic acid by employing a thiamine pyrophosphate-dependent lyase. The corresponding gene is located directly upstream of <i>hcl</i>, which has previously been found only in operonic association with the 2-hydroxyisobutyryl-CoA mutase genes in other bacteria. Heterologous expression of the lyase gene from DSM 45062 in <i>E. coli</i> established a 2-hydroxyisobutyryl-CoA lyase activity in the latter. In line with this, analysis of the DSM 45062 proteome reveals a strong induction of the lyase-HCL gene cluster on 2-HIBA. Acetone is likely degraded via hydroxylation to acetol catalyzed by a MimABCD-related binuclear iron monooxygenase and formic acid appears to be oxidized to CO<sub>2</sub> by selenium-dependent dehydrogenases. The presence of the lyase-HCL gene cluster in isoprene-degrading <i>Rhodococcus</i> strains and <i>Pseudonocardia</i> associated with tropical leafcutter ant species points to a role in degradation of biogenic short-chain ketones and highly branched organic compounds. << Less