Enantioselective hydrolysis of bromo- and methoxy-substituted 1-phenylethanol acetates using carrot and celeriac enzymatic systems.
Enantioselective hydrolysis of bromo- and methoxy-substituted 1-phenylethanol acetates was conducted using comminuted carrot (Daucus carota L.) and celeriac (Apium graveolens L. var. rapaceum) roots. Hydrolysis of the acetates led to alcohols, preferentially to R-(+)-enantiomers. Efficiencies of both reactions - hydrolysis of the acetates with an electron-donating methoxy group and oxidation of the resulting alcohols - increased in the following order: ortho < meta < para. The presence of an electron-withdrawing bromine atom in the aromatic ring had the opposite effect. Oxidation of alcohols with both types of substituents in the aromatic ring showed that location of a substituent had stronger impact on the oxidation rate than its electronic properties.
Maczka
Wanda K
WK
Department of Chemistry, Wrocław University of Environmental and Life Science, ul. Norwida 25, 50-375 Wrocław, Poland.
Mironowicz
Agnieszka
A
D000085:Acetates / Q000378:metabolism; D000438:Alcohols / Q000378:metabolism; D000077102:Apium / Q000201:enzymology*; D018552:Daucus carota / Q000201:enzymology*; D006867:Hydrolases / Q000378:metabolism*; D006868:Hydrolysis; D007700:Kinetics; D010626:Phenylethyl Alcohol / Q000378:metabolism*; D010940:Plant Proteins / Q000378:metabolism; D013237:Stereoisomerism
D000085:Acetates; D000438:Alcohols; D010940:Plant Proteins; D006867:Hydrolases; D010626:Phenylethyl Alcohol