Journal
ORGANIC LETTERS
Volume 23, Issue 12, Pages 4645-4650Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01361
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Funding
- National Key Research and Development Program of China [2020YFA090032, 2019YFA0906200]
- National Natural Science Foundation of China [21907031, 81903529, 21977029, 21877038]
- Open Project Funding of the State Key Laboratory of Bioreactor Engineering
- 111 Project [B18022]
- Shanghai Science and Technology Commission [18JC1411900]
- Japan Society for the Promotion of Science [JP16H06446, 19H02891]
- Natural Science and Engineering Research Council of Canada
- Grants-in-Aid for Scientific Research [19H02891] Funding Source: KAKEN
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Two previously unreported fungal bifunctional terpene synthases, FoFS and AtAS, have been discovered in this study. FoFS catalyzes the formation of fusoxypenes A-C and (-)-astellatene, while AtAS synthesizes preaspterpenacid I. The enantioselective synthesis of sesterterpenes and the cyclization pathways of the fusoxypenes were also characterized.
Genome-based discovery of two previously unreported fungal bifunctional terpene synthases (BFTSs) from phytopathogenic fungi are reported: FoFS catalyzing the formation of fusoxypenes A-C (1-3) and (-)-astellatene (4) and AtAS capable of synthesizing preaspterpenacid I (6). Interestingly, FoFS and AtAS catalyzed the formation of enantiomeric sesterterpenes with a 5-6-7-3-5 ring system. C22-oxidative modification of preaspterpenacid I by AtP450 was characterized as well. Plausible cyclization pathways of the fusoxypenes were illustrated by DFT calculations.
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