article · Biocatalysis and Biotransformation
The efficient asymmetric dihydroxylation of 6,7-epoxygeraniol was performed using a chemoenzymatic \nprocess employing a yeast epoxide hydrolase (EH) resolution stereoinversion step, followed by \nstereoretentive chemical hydrolysis of the remaining epoxide to produce (6 R)-6,7-dihydroxygeraniol \nat unprecedented high enantiometic excess (ee) (>97.5%) and high isolated yield (72 mol % overall \nyield over 5 steps from commercially available geraniol). The enzymatic process was completed \nwithin 2 h at 250 g/L substrate loading reaching > 49.5 mass % conversion of the racemic epoxide. \nThe reaction was self-limiting and furnished both the homochiral (6 R)-triol and the residual (6 R)- \nepoxide at > 99% ee, due to enantio-inversion of the (6S)-epoxide. The (6 R)-epoxide was \nsubsequently chemically hydrolysed, without first needing to separate the epoxide and triol \nproducts, to afford the desired (6 R)-triol product in >97.5% ee, at multigram scale. This \nchemoenzymatic procedure offers an excellent alternative to chemical asymmetric epoxidation or \ndihydroxylation for the production of enantiopure 6,7-dihydroxygeranyl and 6,7-epoxygeranyl type \ncompounds in general. It exemplifies the benefits of using greener EH bioprocesses to produce \nsuch compounds in high ee’s and high isolated yields.
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DOI: 10.1080/10242422.2024.2410780
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