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Artificial farnesol epoxidase enables a concise synthesis of meroterpenoids.

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Title: Artificial farnesol epoxidase enables a concise synthesis of meroterpenoids.
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]
Copyright of Science is the property of American Association for the Advancement of Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Psychology and Behavioral Sciences Collection
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  Data: Artificial farnesol epoxidase enables a concise synthesis of meroterpenoids.
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  Data: <searchLink fieldCode="AR" term="%22Wang%2C+Jinxin%22">Wang, Jinxin</searchLink><br /><searchLink fieldCode="AR" term="%22Yin%2C+Yunpeng%22">Yin, Yunpeng</searchLink><br /><searchLink fieldCode="AR" term="%22Zhang%2C+Quan%22">Zhang, Quan</searchLink><br /><searchLink fieldCode="AR" term="%22Zhang%2C+Wei-Dong%22">Zhang, Wei-Dong</searchLink><br /><searchLink fieldCode="AR" term="%22Li%2C+Jian%22">Li, Jian</searchLink>
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  Data: <searchLink fieldCode="JN" term="%22Science%22">Science</searchLink>. 8/14/2025, Vol. 389 Issue 6761, p732-735. 4p.
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  Data: <searchLink fieldCode="DE" term="%22Farnesol%22">Farnesol</searchLink><br /><searchLink fieldCode="DE" term="%22Terpenes%22">Terpenes</searchLink><br /><searchLink fieldCode="DE" term="%22Enzymatic+analysis%22">Enzymatic analysis</searchLink><br /><searchLink fieldCode="DE" term="%22Alkenes%22">Alkenes</searchLink><br /><searchLink fieldCode="DE" term="%22Epoxidation%22">Epoxidation</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: 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]
– Name: AbstractSuppliedCopyright
  Label:
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  Data: <i>Copyright of Science is the property of American Association for the Advancement of Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1126/science.adt2096
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      – Code: eng
        Text: English
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        PageCount: 4
        StartPage: 732
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      – SubjectFull: Farnesol
        Type: general
      – SubjectFull: Terpenes
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      – SubjectFull: Enzymatic analysis
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      – SubjectFull: Alkenes
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      – SubjectFull: Epoxidation
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              M: 08
              Text: 8/14/2025
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