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A highly efficient chemoenzymatic process to produce (R)-6,7-dihydroxygeraniol.

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Title: A highly efficient chemoenzymatic process to produce (R)-6,7-dihydroxygeraniol.
Authors: Pienaar, Daniel P.1 (AUTHOR) Daniel.Pienaar@up.ac.za, Mitra, Robin K.2,3,4 (AUTHOR), Botes, Adriana L.2,3,4 (AUTHOR), Brady, Dean5 (AUTHOR)
Source: Biocatalysis & Biotransformation. Feb2025, Vol. 43 Issue 1, p109-116. 8p.
Subjects: Epoxide hydrolase, Biochemical substrates, Biocatalysis, Epoxidation, Hydrolysis
Abstract: The efficient asymmetric dihydroxylation of 6,7-epoxygeraniol was performed using a chemoenzymatic process employing a yeast epoxide hydrolase (EH) resolution stereoinversion step, followed by stereoretentive chemical hydrolysis of the remaining epoxide to produce (6 R)-6,7-dihydroxygeraniol at unprecedented high enantiometic excess (ee) (>97.5%) and high isolated yield (72 mol % overall yield over 5 steps from commercially available geraniol). The enzymatic process was completed within 2 h at 250 g/L substrate loading reaching > 49.5 mass % conversion of the racemic epoxide. The reaction was self-limiting and furnished both the homochiral (6 R)-triol and the residual (6 R)-epoxide at > 99% ee, due to enantio-inversion of the (6S)-epoxide. The (6 R)-epoxide was subsequently chemically hydrolysed, without first needing to separate the epoxide and triol products, to afford the desired (6 R)-triol product in >97.5% ee, at multigram scale. This chemoenzymatic procedure offers an excellent alternative to chemical asymmetric epoxidation or dihydroxylation for the production of enantiopure 6,7-dihydroxygeranyl and 6,7-epoxygeranyl type compounds in general. It exemplifies the benefits of using greener EH bioprocesses to produce such compounds in high ee's and high isolated yields. [ABSTRACT FROM AUTHOR]
Copyright of Biocatalysis & Biotransformation is the property of Taylor & Francis Ltd 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.)
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  Data: A highly efficient chemoenzymatic process to produce (R)-6,7-dihydroxygeraniol.
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  Data: <searchLink fieldCode="AR" term="%22Pienaar%2C+Daniel+P%2E%22">Pienaar, Daniel P.</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> Daniel.Pienaar@up.ac.za</i><br /><searchLink fieldCode="AR" term="%22Mitra%2C+Robin+K%2E%22">Mitra, Robin K.</searchLink><relatesTo>2,3,4</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Botes%2C+Adriana+L%2E%22">Botes, Adriana L.</searchLink><relatesTo>2,3,4</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Brady%2C+Dean%22">Brady, Dean</searchLink><relatesTo>5</relatesTo> (AUTHOR)
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  Data: <searchLink fieldCode="JN" term="%22Biocatalysis+%26+Biotransformation%22">Biocatalysis & Biotransformation</searchLink>. Feb2025, Vol. 43 Issue 1, p109-116. 8p.
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  Data: <searchLink fieldCode="DE" term="%22Epoxide+hydrolase%22">Epoxide hydrolase</searchLink><br /><searchLink fieldCode="DE" term="%22Biochemical+substrates%22">Biochemical substrates</searchLink><br /><searchLink fieldCode="DE" term="%22Biocatalysis%22">Biocatalysis</searchLink><br /><searchLink fieldCode="DE" term="%22Epoxidation%22">Epoxidation</searchLink><br /><searchLink fieldCode="DE" term="%22Hydrolysis%22">Hydrolysis</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: The efficient asymmetric dihydroxylation of 6,7-epoxygeraniol was performed using a chemoenzymatic process employing a yeast epoxide hydrolase (EH) resolution stereoinversion step, followed by stereoretentive chemical hydrolysis of the remaining epoxide to produce (6 R)-6,7-dihydroxygeraniol at unprecedented high enantiometic excess (ee) (>97.5%) and high isolated yield (72 mol % overall yield over 5 steps from commercially available geraniol). The enzymatic process was completed within 2 h at 250 g/L substrate loading reaching > 49.5 mass % conversion of the racemic epoxide. The reaction was self-limiting and furnished both the homochiral (6 R)-triol and the residual (6 R)-epoxide at > 99% ee, due to enantio-inversion of the (6S)-epoxide. The (6 R)-epoxide was subsequently chemically hydrolysed, without first needing to separate the epoxide and triol products, to afford the desired (6 R)-triol product in >97.5% ee, at multigram scale. This chemoenzymatic procedure offers an excellent alternative to chemical asymmetric epoxidation or dihydroxylation for the production of enantiopure 6,7-dihydroxygeranyl and 6,7-epoxygeranyl type compounds in general. It exemplifies the benefits of using greener EH bioprocesses to produce such compounds in high ee's and high isolated yields. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: <i>Copyright of Biocatalysis & Biotransformation is the property of Taylor & Francis Ltd 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: 10.1080/10242422.2024.2410780
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      – Code: eng
        Text: English
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      – SubjectFull: Epoxide hydrolase
        Type: general
      – SubjectFull: Biochemical substrates
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      – SubjectFull: Biocatalysis
        Type: general
      – SubjectFull: Epoxidation
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            – D: 01
              M: 02
              Text: Feb2025
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              Y: 2025
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