Biocatalytic Synthesis of Metaxalone and Its Analogues

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 en...

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Bibliographic Details
Published in:Organic letters 2023-07, Vol.25 (27), p.5049-5054
Main Authors: Wang, Zhu-Xiang, Fu, Hong-Kang, Da, Xin-Yu, Wang, Hui-Hui, Cui, Bao-Dong, Han, Wen-Yong, Chen, Yong-Zheng, Wan, Nan-Wei
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01752