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

Publication date: Available online 31 August 2017
Source:Bioorganic & Medicinal Chemistry
Author(s): Katharina Gloria Hugentobler, Michael Müller
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.

Graphical abstract

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