Oxidative dearomatisation: the key step of sorbicillinoid biosynthesis

Ahmed al Fahad, Amira Abood, Katja M. Fisch, Anna Osipow, Jack Davison, Marija Avramovic, Craig P. Butts, Joern Piel, Thomas J. Simpson, Russell J. Cox*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

44 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)523-527
Number of pages5
JournalChemical Science
Volume5
Issue number2
DOIs
Publication statusPublished - 2014

Keywords

  • POLYKETIDE SYNTHASE GENES
  • TRICHODERMA SP USF-2690
  • PENICILLIUM-CHRYSOGENUM
  • VERTICILLIUM-INTERTEXTUM
  • ASPERGILLUS-NIDULANS
  • FUNGAL POLYKETIDE
  • GIBBERELLA-ZEAE
  • CLUSTER
  • PATHWAY
  • SORBICILLACTONE

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