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A flavoprotein dioxygenase steers bacterial tropone biosynthesis via coenzyme A-ester oxygenolysis and ring epoxidation
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4636200
Author(s) Duan Y; Toplak M; Hou A; Brock NL; Dickschat JS; Teufel R
Author(s) at UniBasel Teufel, Robin
Year 2021
Title A flavoprotein dioxygenase steers bacterial tropone biosynthesis via coenzyme A-ester oxygenolysis and ring epoxidation
Journal Journal of the American Chemical Society
Volume 143
Number 27
Pages / Article-Number 10413-10421
Abstract

Bacterial tropone natural products such as tropolone, tropodithietic acid, or the roseobacticides play crucial roles in various terrestrial and marine symbiotic interactions as virulence factors, antibiotics, algaecides, or quorum sensing signals. We now show that their poorly understood biosynthesis depends on a shunt product from aerobic CoA-dependent phenylacetic acid catabolism that is salvaged by the dedicated acyl-CoA dehydrogen-ase-like flavoenzyme TdaE. Further characterization of TdaE revealed an unanticipated complex catalysis, comprising substrate dehydrogenation, noncanonical CoA-ester oxygenolysis, and final ring epoxidation. The enzyme thereby functions as an archetypal flavoprotein dioxygenase that incorporates both oxygen atoms from O-2 into the substrate, most likely involving flavin-N5-peroxide and flavin-N5-oxide species for consecutive CoA-ester cleavage and epoxidation, respectively. The subsequent spontaneous decarboxylation of the reactive enzyme product yields tropolone, which serves as a key virulence factor in rice panicle blight caused by pathogenic edaphic Burkholderia plantarii. Alternatively, the TdaE product is most likely converted to more complex sulfurcontaining secondary metabolites such as tropodithietic acid from predominant marine Rhodobacteraceae (e.g., Phaeobacter inhibens).

Publisher AMER CHEMICAL SOC
ISSN/ISBN 0002-7863
Full Text on edoc
Digital Object Identifier DOI 10.1021/jacs.1c04996
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/34196542
ISI-Number WOS:000674321800043
Document type (ISI) Article
   

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29/03/2024