Flavin-Dependent Monooxygenase-Mediated 1,2-Oxazine Construction <i>via</i> Meisenheimer Rearrangement in the Biosynthesis of Paeciloxazine

Abstract

biochemical assays, site-directed mutations, docking and molecular dynamics simulations, and density functional theory calculations support the mechanism that PaxA first catalyzes N-oxidation to form an N-oxide intermediate, which undergoes [1,2]-Meisenheimer rearrangement with the assistance of an amino acid with proton transfer property. This study expands the repertoire of rearrangement reactions during the biosynthesis of natural products and provides a new strategy for discovering natural products with N-O tethers by genome mining.

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