期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 138, 期 38, 页码 12671-12677出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b08424
关键词
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资金
- Ministry of Education, Culture, Sports, Science and Technology, Japan (JSPS KAKENHI) [JP16H06443, JP15H01836, JP15K16554]
- Tokyo Biochemical Research Foundation
- Noda Institute for Scientific Research
- Sumitomo Foundation
- Grants-in-Aid for Scientific Research [15H01836, 16H06443, 15J12340] Funding Source: KAKEN
Paraherquonin (1), a fungal meroterpenoid produced by Penicillium brasilianum NBRC 6234, possesses a unique, highly congested hexacyclic molecular architecture. Here we identified the biosynthetic gene cluster of 1 (the prh cluster) and elucidated the pathway up to berkeleydione (2), which serves as the key intermediate for the biosynthesis of I as well as many other meroterpenoids. Interestingly, the nonheme iron and a-ketoglutarate-dependent dioxygenase PrhA constructs the cycloheptadiene moiety to afford 2 from preaustinoid A1 (6), probably via the homoallyl-homoallyl radical rearrangement. Additionally, another fungal strain, P. brasilianum MG11, which produces acetoxydehydroaustin instead of 1, was found to have a gene cluster nearly identical to the prh cluster. The dioxygenase encoded by the cluster shares 92% sequence identity with PrhA, and also accepts 6 but produces preaustinoid A3 (17) with a spiro-lactone system, generating a diverging point for the two different meroterpenoid pathways in the same species.
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