Reaction participants Show >> << Hide
- Name help_outline (E)-sinapyl alcohol Identifier CHEBI:64557 (CAS: 537-33-7) help_outline Charge 0 Formula C11H14O4 InChIKeyhelp_outline LZFOPEXOUVTGJS-ONEGZZNKSA-N SMILEShelp_outline COc1cc(cc(OC)c1O)\C=C\CO 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 A Identifier CHEBI:13193 Charge Formula R SMILEShelp_outline * 2D coordinates Mol file for the small molecule Search links Involved in 2,870 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (E)-sinapaldehyde Identifier CHEBI:27949 (Beilstein: 2215799; CAS: 4206-58-0) help_outline Charge 0 Formula C11H12O4 InChIKeyhelp_outline CDICDSOGTRCHMG-ONEGZZNKSA-N SMILEShelp_outline [H]C(=O)\C=C\c1cc(OC)c(O)c(OC)c1 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 AH2 Identifier CHEBI:17499 Charge 0 Formula RH2 SMILEShelp_outline *([H])[H] 2D coordinates Mol file for the small molecule Search links Involved in 2,799 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:76459 | RHEA:76460 | RHEA:76461 | RHEA:76462 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Related reactions help_outline
More general form(s) of this reaction
Publications
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Oxidation of monolignols by members of the berberine bridge enzyme family suggests a role in plant cell wall metabolism.
Daniel B., Pavkov-Keller T., Steiner B., Dordic A., Gutmann A., Nidetzky B., Sensen C.W., van der Graaff E., Wallner S., Gruber K., Macheroux P.
Plant genomes contain a large number of genes encoding for berberine bridge enzyme (BBE)-like enzymes. Despite the widespread occurrence and abundance of this protein family in the plant kingdom, the biochemical function remains largely unexplored. In this study, we have expressed two members of t ... >> More
Plant genomes contain a large number of genes encoding for berberine bridge enzyme (BBE)-like enzymes. Despite the widespread occurrence and abundance of this protein family in the plant kingdom, the biochemical function remains largely unexplored. In this study, we have expressed two members of the BBE-like enzyme family from Arabidopsis thaliana in the host organism Komagataella pastoris. The two proteins, termed AtBBE-like 13 and AtBBE-like 15, were purified, and their catalytic properties were determined. In addition, AtBBE-like 15 was crystallized and structurally characterized by x-ray crystallography. Here, we show that the enzymes catalyze the oxidation of aromatic allylic alcohols, such as coumaryl, sinapyl, and coniferyl alcohol, to the corresponding aldehydes and that AtBBE-like 15 adopts the same fold as vanillyl alcohol oxidase as reported previously for berberine bridge enzyme and other FAD-dependent oxidoreductases. Further analysis of the substrate range identified coniferin, the glycosylated storage form of coniferyl alcohol, as a substrate of the enzymes, whereas other glycosylated monolignols were rather poor substrates. A detailed analysis of the motifs present in the active sites of the BBE-like enzymes in A. thaliana suggested that 14 out of 28 members of the family might catalyze similar reactions. Based on these findings, we propose a novel role of BBE-like enzymes in monolignol metabolism that was previously not recognized for this enzyme family. << Less
J. Biol. Chem. 290:18770-18781(2015) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.