Enzymes
| UniProtKB help_outline | 1 proteins |
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- Name help_outline 3,4-dihydroxystyrene Identifier CHEBI:1390 Charge 0 Formula C8H8O2 InChIKeyhelp_outline FBTSUTGMWBDAAC-UHFFFAOYSA-N SMILEShelp_outline Oc1ccc(C=C)cc1O 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 NADH Identifier CHEBI:57945 (Beilstein: 3869564) help_outline Charge -2 Formula C21H27N7O14P2 InChIKeyhelp_outline BOPGDPNILDQYTO-NNYOXOHSSA-L 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](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 1,136 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
- Name help_outline 4-ethylcatechol Identifier CHEBI:179260 (CAS: 1124-39-6) help_outline Charge 0 Formula C8H10O2 InChIKeyhelp_outline HFLGBNBLMBSXEM-UHFFFAOYSA-N SMILEShelp_outline OC=1C=C(CC)C=CC1O 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 NAD+ Identifier CHEBI:57540 (Beilstein: 3868403) help_outline Charge -1 Formula C21H26N7O14P2 InChIKeyhelp_outline BAWFJGJZGIEFAR-NNYOXOHSSA-M 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](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 1,207 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:73955 | RHEA:73956 | RHEA:73957 | RHEA:73958 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Ethylphenol Formation by Lactobacillus plantarum: Identification of the Enzyme Involved in the Reduction of Vinylphenols.
Santamaria L., Reveron I., de Felipe F.L., de Las Rivas B., Munoz R.
Ethylphenols are strong odorants produced by microbial activity that are described as off flavors in several foods. <i>Lactobacillus plantarum</i> is a lactic acid bacterial species able to produce ethylphenols by the reduction of vinylphenols during the metabolism of hydroxycinnamic acids. Howeve ... >> More
Ethylphenols are strong odorants produced by microbial activity that are described as off flavors in several foods. <i>Lactobacillus plantarum</i> is a lactic acid bacterial species able to produce ethylphenols by the reduction of vinylphenols during the metabolism of hydroxycinnamic acids. However, the reductase involved has not been yet uncovered. In this study, the involvement in vinylphenol reduction of a gene encoding a putative reductase (<i>lp_3125</i>) was confirmed by the absence of reduction activity in the Δ<i>lp_3125</i> knockout mutant. The protein encoded by <i>lp_3125</i>, VprA, was recombinantly produced in <i>Escherichia coli</i> VprA was assayed against vinylphenols (4-vinylphenol, 4-vinylcatechol, and 4-vinylguaiacol), and all were reduced to their corresponding ethylphenols (4-ethylphenol, 4-ethylcatechol, and 4-ethylguaiacol). PCR and high-performance liquid chromatography (HPLC) detection methods revealed that the VprA reductase is not widely distributed among the lactic acid bacteria studied and that only the bacteria possessing the <i>vprA</i> gene were able to produce ethylphenol from vinylphenol. However, all the species belonging to the <i>L. plantarum</i> group were ethylphenol producers. The identification of the <i>L. plantarum</i> VprA protein involved in hydroxycinnamate degradation completes the route of degradation of these compounds in lactic acid bacteria.<b>IMPORTANCE</b> The presence of volatile phenols is considered a major organoleptic defect of several fermented alcoholic beverages. The biosynthesis of these compounds has been mainly associated with <i>Brettanomyces</i>/<i>Dekkera</i> yeasts. However, the potential importance of lactic acid bacteria in volatile phenol spoilage is emphasized by reports describing a faster ethylphenol production by these bacteria than by yeasts. The genetic identification of the bacterial vinylphenol reductase involved in volatile phenol production provides new insights into the role of lactic acid bacteria in the production of these off flavors. The development of a molecular method for the detection of ethylphenol-producing bacteria could be helpful to design strategies to reduce the bacterial production of vinylphenols in fermented foods. << Less
Appl. Environ. Microbiol. 84:e01064-e01064(2018) [PubMed] [EuropePMC]
This publication is cited by 2 other entries.