Bioorganic and Medicinal Chemistry
Bioorganic and Medicinal Chemistry
5 years ago

Towards semisynthetic natural compounds with a biaryl axis: oxidative phenol coupling in Aspergillus niger

Towards semisynthetic natural compounds with a biaryl axis: oxidative phenol coupling in Aspergillus niger
Regio- and stereoselective phenol coupling is difficult to achieve using synthetic strategies. However, in nature, cytochrome P450 enzyme-mediated routes are employed to achieve complete axial stereo- and regiocontrol in the biosynthesis of compounds with potent bioactivity. Here, we report a synthetic biology approach whereby the bicoumarin metabolic pathway in Aspergillus niger was specifically tailored towards the formation of new coupling products. This strategy represents a manipulation of the bicoumarin pathway in A. niger via interchange of the phenol-coupling biocatalyst and could be applied to other components of the pathway to access a variety of atropisomeric natural product derivatives.

Publisher URL: www.sciencedirect.com/science

DOI: S0968089617311434

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