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Halohydrin dehalogenase-catalysed transformations of epifluorohydrin

Biocatalytic ring-opening of epifluorohydrin has been performed by using halohydrin dehalogenase. The enzyme from Mycobacterium sp. GP1 (HheB2) catalysed reaction with high regioselectivity and low enantioselectivity in the presence of different nucleophiles, producing racemic 1- substituted 3-fluoro-2- propanols. No by-products resulting from the ring-closure reaction have been detected, confirming that vicinal fluoro alcohols are not substrates for HHDH. Four different 3- fluoro-2- propanols were prepared under mild reaction conditions starting from epifluorohydrin. High conversions of 85-100% were reached within 1- 3h and depending on the nucleophile used products were isolated in 31-92% yields.

Biocatalysis ; Halohydrin dehalogenase ; Epoxide ring-opening ; Epifluorohydrin ; Fluoro alcohols

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