Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 34, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202206851
Keywords
alpha-Pyrones; beta-Oxidation; Polyketides; Styrylpyrones; Thiolases
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Funding
- Leibniz Association
- Deutsche Forschungs-Gemeinschaft (DFG) [453246485]
- DFG [EXC 2051, 390713860]
- Projekt DEAL
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Enzymes in Escherichia coli can synthesize styrylpyrones with phenylpropionic acids through a non-decarboxylative Claisen condensation, making the reaction more efficient. Different styrylpyrones can also be synthesized in vitro using a cell-free approach. Targeted feeding experiments demonstrate the ability to synthesize these molecules in bacteria.
Naturally occurring alpha-pyrones with biological activities are mostly synthesised by polyketide synthases (PKSs) via iterative decarboxylative Claisen condensation steps. Remarkably, we found that some enzymes related to the fatty acid beta-oxidation pathway in Escherichia coli, namely the CoA ligase FadD and the thiolases FadA and FadI, can synthesise styrylpyrones with phenylpropionic acids in vivo. The two thiolases directly utilise acetyl-CoA as an extender unit for carbon-chain elongation through a non-decarboxylative Claisen condensation, thus making the overall reaction more efficient in terms of carbon and energy consumption. Moreover, using a cell-free approach, different styrylpyrones were synthesised in vitro. Finally, targeted feeding experiments led to the detection of styrylpyrones in other species, demonstrating that the intrinsic ability of the beta-oxidation pathway allows for the synthesis of such molecules in bacteria, revealing an important biological feature hitherto neglected.
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