期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 5, 页码 1658-1661出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201509263
关键词
biosynthesis; domain swapping; prenyltransferases; sesterterpenoids; terpene cyclases
资金
- Ministry of Education, Culture, Sports, Science and Technology, Japan
- Tokyo Biochemical Research Foundation
- Grants-in-Aid for Scientific Research [15K12740, 16H06443, 24688011, 16H06448, 15H03112, 15H01836] Funding Source: KAKEN
Di- and sesterterpene synthases produce C-20 and C-25 isoprenoid scaffolds from geranylgeranyl pyrophosphate (GGPP) and geranylfarnesyl pyrophosphate (GFPP), respectively. By genome mining of the fungus Emericella variecolor, we identified a multitasking chimeric terpene synthase, EvVS, which has terpene cyclase (TC) and prenyltransferase (PT) domains. Heterologous gene expression in Aspergillus oryzae led to the isolation of variediene (1), a novel tricyclic diterpene hydrocarbon. Intriguingly, in vitro reaction with the enzyme afforded the new macrocyclic sesterterpene 2 as a minor product from dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP). The TC domain thus produces the diterpene 1 and the sesterterpene 2 from GGPP and GFPP, respectively. Notably, a domain swap of the PT domain of EvVS with that of another chimeric sesterterpene synthase, EvSS, successfully resulted in the production of 2 in vivo as well. Cyclization mechanisms for the production of these two compounds are proposed.
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