Reaction participants Show >> << Hide
- Name help_outline norrubrofusarin Identifier CHEBI:145839 Charge -1 Formula C14H9O5 InChIKeyhelp_outline RVRLLYKHCMHGKV-UHFFFAOYSA-M SMILEShelp_outline C12=C(C(=C3C(=C1)OC(=CC3=O)C)[O-])C(=CC(=C2)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 O2 Identifier CHEBI:15379 (CAS: 7782-44-7) help_outline Charge 0 Formula O2 InChIKeyhelp_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILEShelp_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,727 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline ustilaginoidin A Identifier CHEBI:145840 Charge -2 Formula C28H16O10 InChIKeyhelp_outline GCSBLYZTGOQVPI-UHFFFAOYSA-L SMILEShelp_outline C12=C(C(=C3C(=C1)OC(=CC3=O)C)[O-])C(=CC(O)=C2C=4C5=C(C(=C6C(=C5)OC(=CC6=O)C)[O-])C(=CC4O)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 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 6,264 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:62688 | RHEA:62689 | RHEA:62690 | RHEA:62691 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Enantioselective phenol coupling by laccases in the biosynthesis of fungal dimeric naphthopyrones.
Obermaier S., Thiele W., Fuertges L., Mueller M.
Biaryl compounds are ubiquitous metabolites that are often formed by dimerization through oxidative phenol coupling. Hindered rotation around the biaryl bond can cause axial chirality. In nature, dimerizations are catalyzed by oxidative enzymes such as laccases. This class of enzymes is known for ... >> More
Biaryl compounds are ubiquitous metabolites that are often formed by dimerization through oxidative phenol coupling. Hindered rotation around the biaryl bond can cause axial chirality. In nature, dimerizations are catalyzed by oxidative enzymes such as laccases. This class of enzymes is known for non-specific oxidase reactions while inherent enantioselectivity is hitherto unknown. Here, we describe four related fungal laccases that catalyze γ-naphthopyrone dimerization in a regio- and atropselective manner. In vitro assays revealed that three enzymes were highly P-selective (ee >95 %), while one enzyme showed remarkable flexibility. Its selectivity for M- or P-configured dimers varied depending on the reaction conditions. For example, a lower enzyme concentration yielded primarily (P)-ustilaginoidin A, whereas the M atropisomer was favored at higher concentration. These results demonstrate inherent enantioselectivity in an enzyme class that was previously thought to comprise only non-selective oxidases. << Less
Angew. Chem. Int. Ed. 58:9125-9128(2019) [PubMed] [EuropePMC]
This publication is cited by 1 other entry.