Artificial farnesol epoxidase enables a concise synthesis of meroterpenoids.
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| Title: | Artificial farnesol epoxidase enables a concise synthesis of meroterpenoids. |
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| Authors: | Wang, Jinxin, Yin, Yunpeng, Zhang, Quan, Zhang, Wei-Dong, Li, Jian |
| Source: | Science. 8/14/2025, Vol. 389 Issue 6761, p732-735. 4p. |
| Subjects: | Farnesol, Terpenes, Enzymatic analysis, Alkenes, Epoxidation |
| Abstract: | Efficient asymmetric epoxidation reactions have been developed for both the head end and tail end double bonds of farnesol, greatly facilitating the synthesis of terpenoid natural products. However, the lack of methods for direct asymmetric epoxidation of the relatively inert internal alkene of farnesol has posed major challenges in the synthesis of many terpenoids. In this study, we describe the engineering of an epoxidase capable of selectively epoxidizing the internal alkene of farnesol with high regioselectivity and enantioselectivity. The resulting epoxidized intermediate has been successfully applied to simplify the synthesis of a variety of meroterpenoids, reducing the total number of synthetic steps by more than half in most cases. Editor's summary: Terpenoids are a large class of natural products that derive from enzymatic modification of terpenes. Wang et al. developed a combined enzymatic and traditional synthetic chemistry approach to generating meroterpenoid compounds. The authors used directed evolution to generate an epoxidase enzyme that is highly selective for the internal olefin of farnesol. The product of this reaction can then be used as an entry point for further modification and cyclization, often cutting synthetic schemes down considerably.—Michael A. Funk [ABSTRACT FROM AUTHOR] |
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| Database: | Psychology and Behavioral Sciences Collection |
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| Abstract: | Efficient asymmetric epoxidation reactions have been developed for both the head end and tail end double bonds of farnesol, greatly facilitating the synthesis of terpenoid natural products. However, the lack of methods for direct asymmetric epoxidation of the relatively inert internal alkene of farnesol has posed major challenges in the synthesis of many terpenoids. In this study, we describe the engineering of an epoxidase capable of selectively epoxidizing the internal alkene of farnesol with high regioselectivity and enantioselectivity. The resulting epoxidized intermediate has been successfully applied to simplify the synthesis of a variety of meroterpenoids, reducing the total number of synthetic steps by more than half in most cases. Editor's summary: Terpenoids are a large class of natural products that derive from enzymatic modification of terpenes. Wang et al. developed a combined enzymatic and traditional synthetic chemistry approach to generating meroterpenoid compounds. The authors used directed evolution to generate an epoxidase enzyme that is highly selective for the internal olefin of farnesol. The product of this reaction can then be used as an entry point for further modification and cyclization, often cutting synthetic schemes down considerably.—Michael A. Funk [ABSTRACT FROM AUTHOR] |
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| ISSN: | 00368075 |
| DOI: | 10.1126/science.adt2096 |
