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The Role of Cytochrome P450 AbyV in the Final Stages of Abyssomicin C Biosynthesis.

Andrew J DevineAlice E ParnellCatherine R BackNicholas R LeesSamuel T JohnsAinul Z ZulkepliRob BarringerKatja ZornJames E M StachMatthew P CrumpMartin A HayesMarc W Van der KampPaul R RaceChristine L Willis
Published in: Angewandte Chemie (Weinheim an der Bergstrasse, Germany) (2022)
Abyssomicin C and its atropisomer are potent inhibitors of bacterial folate metabolism. They possess complex polycyclic structures, and their biosynthesis has been shown to involve several unusual enzymatic transformations. Using a combination of synthesis and in vitro assays we reveal that AbyV, a cytochrome P450 enzyme from the aby gene cluster, catalyses a key late-stage epoxidation required for the installation of the characteristic ether-bridged core of abyssomicin C. The X-ray crystal structure of AbyV has been determined, which in combination with molecular dynamics simulations provides a structural framework for our functional data. This work demonstrates the power of combining selective carbon-13 labelling with NMR spectroscopy as a sensitive tool to interrogate enzyme-catalysed reactions in vitro with no need for purification.
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