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- Name help_outline (E)-4-oxonon-2-en-1-ol Identifier CHEBI:142624 Charge 0 Formula C9H16O2 InChIKeyhelp_outline GLYROUYLKGPVGY-FNORWQNLSA-N SMILEShelp_outline C(/C=C/C(CCCCC)=O)O 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline NADP+ Identifier CHEBI:58349 Charge -3 Formula C21H25N7O17P3 InChIKeyhelp_outline XJLXINKUBYWONI-NNYOXOHSSA-K SMILEShelp_outline NC(=O)c1ccc[n+](c1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,285 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (E)-4-oxonon-2-enal Identifier CHEBI:58972 (Beilstein: 4963551; CAS: 103560-62-9) help_outline Charge 0 Formula C9H14O2 InChIKeyhelp_outline SEPPVOUBHWNCAW-FNORWQNLSA-N SMILEShelp_outline CCCCCC(=O)\C=C\C=O 2D coordinates Mol file for the small molecule Search links Involved in 1 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 NADPH Identifier CHEBI:57783 (Beilstein: 10411862) help_outline Charge -4 Formula C21H26N7O17P3 InChIKeyhelp_outline ACFIXJIJDZMPPO-NNYOXOHSSA-J SMILEShelp_outline NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]2O)n2cnc3c(N)ncnc23)[C@@H](O)[C@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1,279 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:58432 | RHEA:58433 | RHEA:58434 | RHEA:58435 | |
|---|---|---|---|---|
| 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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Role of human aldo-keto-reductase AKR1B10 in the protection against toxic aldehydes.
Martin H.J., Maser E.
Damage of cell membranes by reactive oxygen species results in the formation of toxic lipid peroxides which may ultimately lead to cell death. Among the best characterized intermediates of oxidative stress are the unsaturated aldehydes 4-hydroxynon-2-enal (4-HNE) and its oxidized counterpart 4-oxo ... >> More
Damage of cell membranes by reactive oxygen species results in the formation of toxic lipid peroxides which may ultimately lead to cell death. Among the best characterized intermediates of oxidative stress are the unsaturated aldehydes 4-hydroxynon-2-enal (4-HNE) and its oxidized counterpart 4-oxonon-2-enal (4-ONE). 4-HNE has been linked to various pathological conditions including atherosclerosis, Parkinson's and Alzheimer's disease. 4-Methylpentanal (4-MP) is a side-chain cleavage product formed endogenously during steroidogenesis from cholesterol. Like 4-HNE and 4-ONE, 4-MP is capable of binding covalently to and cross-linking of proteins. These aldehydes are also damaging DNA by the formation of adducts. We found that AKR1B10, a cytosolic member of the aldo-keto reductase superfamily, efficiently catalyzes the reduction of 4-HNE (K(m)=0.3mM, k(cat)=43 min(-1)), 4-ONE (K(m)=0.3mM, k(cat)=40 min(-1)) and 4-MP (K(m)=0.05 mM, k(cat)=25 min(-1)). AKR1B10 catalyzed 4-MP reduction with a 30-fold increase in activity using NADPH as cofactor compared with NADH. As was observed for aldose reductase (AKR1B1) 4-ONE rapidly inactivates AKR1B10, while this inactivation is not observed when the enzyme is pre-incubated with NADPH. It was shown that cysteine 298 of aldose reductase was protected by NADPH from the alpha,beta-unsaturated carbonyls of 4-ONE thus rendering resistance towards inactivation. We generated a mutant AKR1B10, changing the respective cysteine on position 299 of AKR1B10 into a serine. This C299S mutant is still active towards 4-HNE and 4-ONE, albeit at a somewhat lower catalytic efficiency. However, it is still inactivated by 4-ONE in the absence of NADPH.While the best substrates for AKR1B10 are retinals, the high catalytic efficiency together with the protection from inactivation by NADPH suggests a role of AKR1B10 in the detoxification of biogenic aldehydes. << Less
Chem. Biol. Interact. 178:145-150(2009) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.