西亚试剂：Flavin-mediated dual oxidation controls an enzymatic Favors

Flavin-mediated dual oxidation controls an enzymatic Favorskii-type rearrangement

Robin Teufel，Akimasa Miyanaga，Quentin Michaudel，Frederick Stull，Gordon Louie，Joseph P. Bruce Palfey& Bradley S. Moore

Flavoproteins catalyse a diversity of fundamental redox reactions and are one of the most studied enzyme families1， 2. As monooxygenases， they are universally thought to control oxygenation by means of a peroxyflavin species that transfers a single atom of molecular oxygen to an organic substrate1， 3， 4. Here we report that the bacterial flavoenzyme EncM5， 6 catalyses the peroxyflavin-independent oxygenation–dehydrogenation dual oxidation of a highly reactive poly(β-carbonyl). The crystal structure of EncM with bound substrate mimics and isotope labelling studies reveal previously unknown flavin redox biochemistry. We show that EncM maintains an unexpected stable flavin-oxygenating species， proposed to be a flavin-N5-oxide， to promote substrate oxidation and trigger a rare Favorskii-type rearrangement that is central to the biosynthesis of the antibiotic enterocin. This work provides new insight into the fine-tuning of the flavin cofactor in offsetting the innate reactivity of a polyketide substrate to direct its efficient electrocyclization.

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