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. |
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| 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] |
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| Database: | Engineering Source |
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| 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] |
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| ISSN: | 10242422 |
| DOI: | 10.1080/10242422.2024.2410780 |
