Enantiomeric hydrophobic alcohols

Production of Enantiomerically Pure Hydrophobic Alcohols Comparison of Different Process Routes and Reactor Configurations 556... 

For the production of chiral hydrophobic alcohols, FDH from C. boidinii was combined with an NAD+-dependent alcohol dehydrogenase (ADH) from Rhodo-coccus erythropolis. As a first example for the production of hydrophobic alcohols, an enzyme membrane reactor (EMR) was used for the synthesis enantiomerically pure (S)-1 -phenylpropan-2-ol and some related structures out of their corresponding ketones [42]. 

We Umit this section to a discussion of stereochemical studies that sought to demonstrate discriminating enantiomeric interactions in monolayers of simple surfactants having one hydrophobic chain of methylenes and, generally, a single chiral center. Work in this area includes derivatives of long chain fatty acids, alcohols, or esters whose chiral center is included in the methylene chain. 

The lipase-catalyzed resolutions usually are performed with racemic secondary alcohols in the presence of an acyl donor in hydrophobic organic solvents such as toluene and tert-butyl methyl ether (Scheme 1.3). In case the enzyme is highly enantioselective E = 200 or greater), the resolution reaction in general is stopped at nearly 50% conversion to obtain both unreacted enantiomers and acylated enantiomers in enantiomerically enriched forms. With a moderately enantioselective enzyme E = 20-50), the reaction carries to well over 50% conversion to get unreacted enantiomer of high optical purity at the cost of acylated enantiomer of lower optical purity. The enantioselectivity of lipase is largely dependent on the structure of substrate as formulated by Kazlauskas [6] most lipases show... 

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