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EnglishWe applied Horse Liver Alcohol Dehydrogenase (HLADH) to the enantioselective synthesis of six (2S)-2-arylpropanols, useful intermediates in the synthesis of Profens. The influence of substrate structure and reaction conditions on yields and enantioselectivity were investigated. The high yields and high enantioselectivity towards the (S)-enantiomer obtained in the bioreduction of 2-arylpropionic aldehydes, clearly indicate the achievement of a DKR process through a combination of an enzyme-catalyzed kinetic reduction with a chemical base-catalyzed racemization of the unreacted aldehydes. The racemization step is represented by the keto–enol equilibrium of the aldehyde and can be controlled by modulating pH and reaction conditions.
| Titolo: | Chemoenzymatic synthesis of (2S)-2-arylpropanols through a dynamic kinetic resolution of 2-arylpropanals with alcohol dehydrogenases | |
| Autore/i: | GALLETTI, PAOLA; EMER, ENRICO; G. Gucciardo; QUINTAVALLA, ARIANNA; PORI, MATTEO; GIACOMINI, DARIA | |
| Autore/i Unibo: | ||
| Anno: | 2010 | |
| Rivista: | ||
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1039/c005098a | |
| Abstract: | We applied Horse Liver Alcohol Dehydrogenase (HLADH) to the enantioselective synthesis of six (2S)-2-arylpropanols, useful intermediates in the synthesis of Profens. The influence of substrate structure and reaction conditions on yields and enantioselectivity were investigated. The high yields and high enantioselectivity towards the (S)-enantiomer obtained in the bioreduction of 2-arylpropionic aldehydes, clearly indicate the achievement of a DKR process through a combination of an enzyme-catalyzed kinetic reduction with a chemical base-catalyzed racemization of the unreacted aldehydes. The racemization step is represented by the keto–enol equilibrium of the aldehyde and can be controlled by modulating pH and reaction conditions. | |
| Data prodotto definitivo in UGOV: | 2010-09-01 15:29:32 | |
| Appare nelle tipologie: | 1.01 Articolo in rivista |
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