Biocatalytic Synthesis of Metaxalone and Its Analogues

Abstract

A biocatalytic approach for the synthesis of metaxalone and its analogues was developed based on the reaction of epoxides and cyanate catalyzed by halohydrin dehalogenase. Gram-scale synthesis of chiral and racemic metaxalone was achieved with 44% (98% ee ) and 81% yields, respectively, by protein engineering of the halohydrin dehalogenase HHDHamb from Acidimicrobiia bacterium . Additionally, various metaxalone analogues were synthesized at 28–40% yields (90–99% ee ) for chiral forms and 77–92% yields for racemic forms.

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