Monapinone Coupling Enzyme Produces Non-Natural Heterodimers

The monapinone coupling enzyme (MCE), a fungal multicopper oxidase, catalyzes the regioselective C–C between tricyclic A (the primary substrate) and other monapinones (secondary substrates) to produce atropisomeric biaryl homo- or heterodimers. In this study, mono-, bi- compounds were tested determine whether they worked as secondary substrates for MCE. Among 14 cyclic compounds, MCE utilized semivioxanthin, YWA1, 1,3-naphthalenediol flaviolin non-natural heterodimers produced by from semivioxanthin isolated, their structures elucidated NMR MS. These findings indicate that recognizes with 1,3-dihydroxy 1-hydroxy-3-methoxy benzene ring substrate.