Reaction participants Show >> << Hide
- 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 2,713 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline methyl 2-[(3S)-9,10-dihydroxy-7-methoxy-1-oxo-1H,3H,4H-naphtho[2,3-c]pyran-3-yl]acetate Identifier CHEBI:146012 Charge 0 Formula C17H14O7 InChIKeyhelp_outline MPGOVJDYMMGUQB-UHFFFAOYSA-N SMILEShelp_outline C=12C(=C3C(=CC(=CC3=CC1C=C(OC2=O)CC(OC)=O)OC)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 A Identifier CHEBI:13193 Charge Formula R SMILEShelp_outline * 2D coordinates Mol file for the small molecule Search links Involved in 2,783 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline semiviriditoxin Identifier CHEBI:146008 Charge 0 Formula C17H16O7 InChIKeyhelp_outline CVDVPYTVGZWTON-NSHDSACASA-N SMILEShelp_outline C=12C(=C3C(=CC(=CC3=CC1C[C@H](OC2=O)CC(OC)=O)OC)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
Cross-references
| RHEA:62876 | RHEA:62877 | RHEA:62878 | RHEA:62879 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
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Publications
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Fungal dirigent protein controls the stereoselectivity of multicopper oxidase-catalyzed phenol coupling in viriditoxin biosynthesis.
Hu J., Li H., Chooi Y.H.
Paecilomyces variotii produces the antibacterial and cytotoxic ( M)-viriditoxin (1) together with a trace amount of its atropisomer ( P)-viriditoxin 1'. Elucidation of the biosynthesis by heterologous pathway reconstruction in Aspergillus nidulans identified the multicopper oxidase (MCO) VdtB resp ... >> More
Paecilomyces variotii produces the antibacterial and cytotoxic ( M)-viriditoxin (1) together with a trace amount of its atropisomer ( P)-viriditoxin 1'. Elucidation of the biosynthesis by heterologous pathway reconstruction in Aspergillus nidulans identified the multicopper oxidase (MCO) VdtB responsible for the regioselective 6,6'-coupling of semiviriditoxin (10), which yielded 1 and 1' at a ratio of 1:2. We further uncovered that VdtD, an α/β hydrolase-like protein lacking the catalytic serine, directs the axial chirality of the products. Using recombinant VdtB and VdtD as cell-free extracts from A. nidulans, we demonstrated that VdtD acts like a dirigent protein to control the stereoselectivity of the coupling catalyzed by VdtB to yield 1 and 1' at a ratio of 20:1. Furthermore, we uncovered a unique Baeyer-Villiger monooxygenase (BVMO) VdtE that could transform the alkyl methylketone side chain to methyl ester against the migratory aptitude. << Less
J. Am. Chem. Soc. 141:8068-8072(2019) [PubMed] [EuropePMC]
This publication is cited by 6 other entries.