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Enantioselective Hydrolysis of Functionalized 2,2‐Disubstituted Oxiranes with Bacterial Epoxide Hydrolases
Author(s) -
Steinreiber Andreas,
Osprian Ingrid,
Mayer Sandra F.,
Orru Romano V. A.,
Faber Kurt
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200011)2000:22<3703::aid-ejoc3703>3.0.co;2-3
Subject(s) - chemistry , enantioselective synthesis , stereocenter , epoxide , epoxide hydrolase , ether , biocatalysis , hydrolysis , side chain , selectivity , stereochemistry , substrate (aquarium) , vicinal , organic chemistry , catalysis , enzyme , reaction mechanism , polymer , microsome , oceanography , geology
The biohydrolysis of 2,2‐disubstituted oxiranes bearing various oxygen functional groups was investigated using the epoxide hydrolase activity of 11 bacterial strains. The results show that the activity and the selectivity strongly depend on the substrate structure and the biocatalyst. Whereas substrates possessing free hydroxyl groups were not transformed, their analogs, protected as ethers, were well accepted. This allowed the convenient modulation of the enantioselectivity by proper choice of the ether group according to size and polarity. It was found that the distance of the ether‐oxygen to the stereogenic quaternary carbon center of the oxirane ring had a profound influence on the enantioselectivity, and several oxiranes were resolved with good to excellent selectivities. The enantiomerically enriched epoxides and vicinal diols thus obtained contain a useful “synthetic handle” in their side chain, which allows their use as building blocks in asymmetric synthesis.