期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 13, 页码 7042-7048出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b03220
关键词
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资金
- Ministry of Education, Culture, Sports, Science and Technology, Japan (JSPS KAKENHI) [JP15H01835, JP16H03277, JP16H06446]
- Grants-in-Aid for Scientific Research [16H06446, 15H01835, 16H03277] Funding Source: KAKEN
The total biosynthesis of (-)-terpestacin was achieved by heterologous expression of four biosynthetic enzyme genes (tpcA-D) in Aspergillus oryzae. After construction of preterpestacin I by the action of bifunctional terpene synthase (TpcA), two cytochrome P450s (TpcBC) activate inert C-H bond to install three hydroxyl groups on the A-ring in stereo- and regioselective manners. Subsequently, a flavin-dependent oxidase (TpcD) catalyzes oxidation of the vicinal diol moiety to give a alpha-diketone, which undergoes an enolization to furnish terpestacin. The successful synthesis of structurally elaborated terpestacin showed that a reconstitution approach that harnesses several biosynthetic enzyme genes in A. oryzae could be a promising alternative to the current chemical synthesis of natural terpenoids.
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