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Chem Sci. 2014 Feb 23;5(2):523-527. Epub 2013 Nov 26.

Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis†Electronic supplementary information (ESI) available: Containing all experimental details. See DOI: 10.1039/c3sc52911hClick here for additional data file.

Author information

1
School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , UK . Email: r.j.cox@bris.ac.uk ; ; Tel: +44 (0) 117 928 9184.
2
School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , UK . Email: r.j.cox@bris.ac.uk ; ; Tel: +44 (0) 117 928 9184 ; Chemistry of Natural and Microbial Products , National Research Centre , Dokki , Egypt.
3
Institute of Microbiology , Eidgenössische Technische Hochschule (ETH) Zürich , Wolfgang-Pauli-Str. 10 , 8093 Zürich , Switzerland.
4
Institute of Microbiology , Eidgenössische Technische Hochschule (ETH) Zürich , Wolfgang-Pauli-Str. 10 , 8093 Zürich , Switzerland ; Kekulé Institute of Organic Chemistry and Biochemistry , University of Bonn , Gerhard-Domagk-Str. 1 , 53121 Bonn , Germany.
5
School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , UK . Email: r.j.cox@bris.ac.uk ; ; Tel: +44 (0) 117 928 9184 ; Institut für Organische Chemie , Leibniz Universität Hannover , Schneiderberg 1B , 30167 Hannover , Germany . Email: russell.cox@oci.uni-hannover.de.

Abstract

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.

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