โ Scribed by M. Mischitz; W. Kroutil; U. Wandel; K. Faber
No coin nor oath required. For personal study only.
Kinetic resolution of 2-mono-and 2,2-disubstituted epoxides was accomplished using epoxide hydrolases from bacterial and fungal origin by employing lyophilized whole microbial cells. In all cases investigated, the biocatalytic hydrolysis was shown to proceed with retention of configuration at the stereogenic center leading to 1,2-diols and remaining epoxides.
The selectivity of the reaction was dependent on the substrate structure and the slxain used with E-values ranging from low or moderate (with 2-monosubstituted epoxides) to excellent (E >100, with 2,2-disubstituted oxiranes).
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Epoxide hydrolases from bacterial and fungal sources are highly versatile biocatalysts for the asymmetric hydrolysis of epoxides on a preparative scale. Besides kinetic resolution, which yields the corresponding enantiomerically enriched vicinal diol and the remaining nonconverted epoxide, enantioco
## Abstract Safety and regulatory issues favor increasing use of enantiopure compounds in pharmaceuticals. Enantiopure epoxides and diols are valuable intermediates in organic synthesis for the production of optically active pharmaceuticals. Enantiopure epoxide can be prepared using epoxide hydrola