Issue 2, 2014

Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis


An FAD-dependent monooxygenase encoding gene (SorbC) was cloned from Penicillium chrysogenum E01-10/3 and expressed as a soluble protein in Escherichia coli. The enzyme efficiently performed the oxidative dearomatisation of sorbicillin and dihydrosorbicillin to give sorbicillinol and dihydrosorbicillinol respectively. Bioinformatic examination of the gene cluster surrounding SorbC indicated the presence of two polyketide synthase (PKS) encoding genes designated sorbA and sorbB. The gene sorbA-encodes a highly reducing iterative PKS while SorbB encodes a non-reducing iterative PKS which features a reductive release domain usually involved in the production of polyketide aldehydes. Using these observations and previously reported results from isotopic feeding experiments a new and simpler biosynthetic route to the sorbicillin class of secondary metabolites is proposed which is consistent with all reported experimental results.

Graphical abstract: Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis

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Article information

Article type
Edge Article
21 Oct 2013
15 Nov 2013
First published
20 Nov 2013
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2014,5, 523-527

Author version available

Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis

A. A. Fahad, A. Abood, K. M. Fisch, A. Osipow, J. Davison, M. Avramović, C. P. Butts, J. Piel, T. J. Simpson and R. J. Cox, Chem. Sci., 2014, 5, 523 DOI: 10.1039/C3SC52911H

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