Enantioselective Hydrolysis of Bromo- and Methoxy-Substituted 1-Phenylethanol Acetates Using Carrot and Celeriac Enzymatic Systems

Abstract

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 electrondonating 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.

Vegetables as biocatalysts in stereoselective hydrolysis of labile organic compounds

“…NMR data corresponded with published data. 30 (15), 97 (14), 86(37), 70 (18), 69 (11), 59 (16), 57(100), 55 (15). 5-Hydroxy-3-heptanone (2).…”

“…The diastereomeric identification is tentative, but based on Heathcock's empirical rule 36 in addition to relative intensities of peaks in 1 H-NMR spectrum in relation to relative areas of GC chromatograms. GCMS: 154 (11), 143 (18), 114 (26), 99 (29), 86 (15), 84 (14), 83 (13), 71(100), 69 (13), 59 (19), 58 (11), 57 (16), 56 (13), 55 (20), 43(47), 41 (18).…”