Reaction participants Show >> << Hide
- 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 2,709 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
- Name help_outline (M)-viriditoxin Identifier CHEBI:146007 (CAS: 1381782-08-6) help_outline Charge 0 Formula C34H30O14 InChIKeyhelp_outline GMCZVCXZGZGZPX-HOTGVXAUSA-N SMILEShelp_outline C=12C(=C3C(=CC(=C(C3=CC1C[C@H](OC2=O)CC(OC)=O)C=4C5=CC6=C(C(=C5C(=CC4OC)O)O)C(O[C@@H](C6)CC(OC)=O)=O)OC)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 (Beilstein: 3587155; 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 6,204 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:62884 | RHEA:62885 | RHEA:62886 | RHEA:62887 | |
|---|---|---|---|---|
| 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.