Enzymes
| UniProtKB help_outline | 2 proteins |
Reaction participants Show >> << Hide
- Name help_outline 4-O-β-D-glucosyl-trans-ferulate Identifier CHEBI:141767 Charge -1 Formula C16H19O9 InChIKeyhelp_outline IEMIRSXOYFWPFD-BJGSYIFTSA-M SMILEShelp_outline C=1C=C(C=C(C1O[C@@H]2O[C@@H]([C@H]([C@@H]([C@H]2O)O)O)CO)OC)/C=C/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 H2O Identifier CHEBI:15377 (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 6,485 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 4-O-β-D-glucosyl-vanillin Identifier CHEBI:179508 (CAS: 494-08-6) help_outline Charge 0 Formula C14H18O8 InChIKeyhelp_outline LPRNQMUKVDHCFX-RKQHYHRCSA-N SMILEShelp_outline O1[C@@H]([C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC2=C(OC)C=C(C=C2)C=O)CO 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 acetate Identifier CHEBI:30089 (CAS: 71-50-1) help_outline Charge -1 Formula C2H3O2 InChIKeyhelp_outline QTBSBXVTEAMEQO-UHFFFAOYSA-M SMILEShelp_outline CC([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 182 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:76503 | RHEA:76504 | RHEA:76505 | RHEA:76506 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
|
|||
| EC numbers help_outline | ||||
| MetaCyc help_outline |
Publications
-
Vanillin formation from ferulic acid in Vanilla planifolia is catalysed by a single enzyme.
Gallage N.J., Hansen E.H., Kannangara R., Olsen C.E., Motawia M.S., Joergensen K., Holme I., Hebelstrup K., Grisoni M., Moeller B.L.
Vanillin is a popular and valuable flavour compound. It is the key constituent of the natural vanilla flavour obtained from cured vanilla pods. Here we show that a single hydratase/lyase type enzyme designated vanillin synthase (VpVAN) catalyses direct conversion of ferulic acid and its glucoside ... >> More
Vanillin is a popular and valuable flavour compound. It is the key constituent of the natural vanilla flavour obtained from cured vanilla pods. Here we show that a single hydratase/lyase type enzyme designated vanillin synthase (VpVAN) catalyses direct conversion of ferulic acid and its glucoside into vanillin and its glucoside, respectively. The enzyme shows high sequence similarity to cysteine proteinases and is specific to the substitution pattern at the aromatic ring and does not metabolize caffeic acid and p-coumaric acid as demonstrated by coupled transcription/translation assays. VpVAN localizes to the inner part of the vanilla pod and high transcript levels are found in single cells located a few cell layers from the inner epidermis. Transient expression of VpVAN in tobacco and stable expression in barley in combination with the action of endogenous alcohol dehydrogenases and UDP-glucosyltransferases result in vanillyl alcohol glucoside formation from endogenous ferulic acid. A gene encoding an enzyme showing 71% sequence identity to VpVAN was identified in another vanillin-producing plant species Glechoma hederacea and was also shown to be a vanillin synthase as demonstrated by transient expression in tobacco. << Less
Nat. Commun. 5:4037-4037(2014) [PubMed] [EuropePMC]
This publication is cited by 5 other entries.
Comments
Multi-step reaction: RHEA:79443 and RHEA:79447