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Asymmetric photoenzymatic incorporation of fluorinated motifs into olefins.

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Title: Asymmetric photoenzymatic incorporation of fluorinated motifs into olefins.
Authors: Maolin Li, Yujie Yuan, Harrison, Wesley, Zhengyi Zhang, Huimin Zhao
Source: Science (pre-March 2025). 7/26/2024, Vol. 385 Issue 6707, p416-421. 6p. 4 Diagrams.
Subjects: Alkenes, Hydrogen atom, Biosynthesis, Promiscuity, Agricultural chemicals
Abstract: Enzymes capable of assimilating fluorinated feedstocks are scarce. This situation poses a challenge for the biosynthesis of fluorinated compounds used in pharmaceuticals, agrochemicals, and materials. We developed a photoenzymatic hydrofluoroalkylation that integrates fluorinated motifs into olefins. The photoinduced promiscuity of flavin-dependent ene-reductases enables the generation of carbon-centered radicals from iodinated fluoroalkanes, which are directed by the photoenzyme to engage enantioselectively with olefins. This approach facilitates stereocontrol through interaction between a singular fluorinated unit and the enzyme, securing high enantioselectivity at β, γ, or δ positions of fluorinated groups through enzymatic hydrogen atom transfer—a process that is notably challenging with conventional chemocatalysis. This work advances enzymatic strategies for integrating fluorinated chemical feedstocks and opens avenues for asymmetric synthesis of fluorinated compounds. [ABSTRACT FROM AUTHOR]
Copyright of Science (pre-March 2025) 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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PubType: Academic Journal
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  Data: Asymmetric photoenzymatic incorporation of fluorinated motifs into olefins.
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  Data: <searchLink fieldCode="AR" term="%22Maolin+Li%22">Maolin Li</searchLink><br /><searchLink fieldCode="AR" term="%22Yujie+Yuan%22">Yujie Yuan</searchLink><br /><searchLink fieldCode="AR" term="%22Harrison%2C+Wesley%22">Harrison, Wesley</searchLink><br /><searchLink fieldCode="AR" term="%22Zhengyi+Zhang%22">Zhengyi Zhang</searchLink><br /><searchLink fieldCode="AR" term="%22Huimin+Zhao%22">Huimin Zhao</searchLink>
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  Data: <searchLink fieldCode="JN" term="%22Science+%28pre-March+2025%29%22">Science (pre-March 2025)</searchLink>. 7/26/2024, Vol. 385 Issue 6707, p416-421. 6p. 4 Diagrams.
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  Data: <searchLink fieldCode="DE" term="%22Alkenes%22">Alkenes</searchLink><br /><searchLink fieldCode="DE" term="%22Hydrogen+atom%22">Hydrogen atom</searchLink><br /><searchLink fieldCode="DE" term="%22Biosynthesis%22">Biosynthesis</searchLink><br /><searchLink fieldCode="DE" term="%22Promiscuity%22">Promiscuity</searchLink><br /><searchLink fieldCode="DE" term="%22Agricultural+chemicals%22">Agricultural chemicals</searchLink>
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  Data: Enzymes capable of assimilating fluorinated feedstocks are scarce. This situation poses a challenge for the biosynthesis of fluorinated compounds used in pharmaceuticals, agrochemicals, and materials. We developed a photoenzymatic hydrofluoroalkylation that integrates fluorinated motifs into olefins. The photoinduced promiscuity of flavin-dependent ene-reductases enables the generation of carbon-centered radicals from iodinated fluoroalkanes, which are directed by the photoenzyme to engage enantioselectively with olefins. This approach facilitates stereocontrol through interaction between a singular fluorinated unit and the enzyme, securing high enantioselectivity at β, γ, or δ positions of fluorinated groups through enzymatic hydrogen atom transfer—a process that is notably challenging with conventional chemocatalysis. This work advances enzymatic strategies for integrating fluorinated chemical feedstocks and opens avenues for asymmetric synthesis of fluorinated compounds. [ABSTRACT FROM AUTHOR]
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  Data: <i>Copyright of Science (pre-March 2025) 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.)
PLink https://search.ebscohost.com/login.aspx?direct=true&site=eds-live&db=pbh&AN=178671931
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        Value: 10.1126/science.adk8464
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        Text: English
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        Type: general
      – SubjectFull: Hydrogen atom
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      – SubjectFull: Biosynthesis
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      – SubjectFull: Agricultural chemicals
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              M: 07
              Text: 7/26/2024
              Type: published
              Y: 2024
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