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. 2020 Nov 2;59(45):19961-19965.
doi: 10.1002/anie.202010084. Epub 2020 Aug 31.

The Biosynthetic Gene Cluster for Sestermobaraenes-Discovery of a Geranylfarnesyl Diphosphate Synthase and a Multiproduct Sesterterpene Synthase from Streptomyces mobaraensis

Anwei Hou  1 , Jeroen S Dickschat  1
Affiliations

The Biosynthetic Gene Cluster for Sestermobaraenes-Discovery of a Geranylfarnesyl Diphosphate Synthase and a Multiproduct Sesterterpene Synthase from Streptomyces mobaraensis

Anwei Hou et al. Angew Chem Int Ed Engl. .

Abstract

A biosynthetic gene cluster from Streptomyces mobaraensis encoding the first cases of a bacterial geranylfarnesyl diphosphate synthase and a type I sesterterpene synthase was identified. The structures of seven sesterterpenes produced by these enzymes were elucidated, including their absolute configurations. The enzyme mechanism of the sesterterpene synthase was investigated by extensive isotope labeling experiments.

Keywords: Streptomyces mobaraensis; biosynthetic gene cluster; configuration determination; enzyme catalysis; terpenes.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Bacterial sesterterpenes and the fungal compound ophiobolin F (5).
Figure 2
Figure 2
Clustered genes for a GFPPS (turquoise) and SmTS1 (pink) in S. mobaraensis.
Scheme 1
Scheme 1
Biosynthesis of sestermobaraenes and sestermobaraol by SmTS1 in S. mobaraensis.
Scheme 2
Scheme 2
The absolute configurations of 6–12, by enantioselective deuteration (HR=2H or HS=2H; HE=2H or HZ=2H). Numbers at C and H atoms indicate chemical shifts for unlabeled 6–12.
See this image and copyright information in PMC

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