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Title:Enantioselective Epoxidation of Alkenes by Chloroperoxidase and the Development of a Chloroperoxidase Expression System
Author(s):Allain, Eric Joseph
Doctoral Committee Chair(s):Hager, Lowell P.
Department / Program:Biochemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Subject(s):Chemistry, Organic
Abstract:Chloroperoxidase from Caldariomyces fumago has the characteristics of a promising industrial catalyst. Chloroperoxidase is inexpensive to produce and relatively stable and able to catalyze a large number of potentially useful reactions. However, the majority of the reactions studied occur with a lack of any enzyme induced stereoselectivity. Chloroperoxidase, in this report, is shown to catalyze the epoxidation reaction of a number of alkenes in a highly enantioselective manner with enantiomeric excesses between 50% and 97%. Good substrates were generally non-polar cis-alkenes of less than nine carbons in length. Unsubstituted terminal alkenes were shown to inactivate the enzyme. The recent determination of the three dimensional structure by x-ray crystallography and ongoing research in the development of an expression system for chloroperoxidase could open the door for a number of experiments concerning the mechanism of the epoxidation reaction. Also the possibility of improving the utility of chloroperoxidase in asymmetric epoxidations through directed evolution and site-directed mutagenesis remains an exciting prospect for the future.
Issue Date:1997
Description:94 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1997.
Other Identifier(s):(MiAaPQ)AAI9717245
Date Available in IDEALS:2015-09-25
Date Deposited:1997

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