Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 349, Issue 14-15, Pages 2279-2285Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200700146
Keywords
azides; cyanides; epoxides; halohydrin; dehalogenase; kinetic resolution; tertiary alcohols
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The halohydrin dehalogenase from Agrobacterium radiobacter AD1 (HheC) catalyzes nucleophilic ring opening of epoxides with cyanide and azide. In the case of 2,2-disubstituted epoxides, this reaction proceeds with excellent enantioselectivity (E values up to > 200), which gives, by kinetic resolution, access to various enantiopure epoxides and beta-substituted tertiary alcohols (ee up to 99%). Since the enzyme has a broad substrate range and because these tertiary alcohols are difficult to prepare in other ways, HheC is an attractive biocatalyst for the production of P-cyano and P-azido tertiary alcohols.
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