Chemoenzymatic synthesis of (2S)-2-arylpropanols through a dynamic kinetic resolution of 2-arylpropanals with alcohol dehydrogenases.
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.
Galletti
Paola
P
Department of Chemistry G. Ciamician, University of Bologna, Via Selmi 2, Bologna, I-40126, Italy. paola.galletti@unibo.it
Emer
Enrico
E
Gucciardo
Gabriele
G
Quintavalla
Arianna
A
Pori
Matteo
M
Giacomini
Daria
D
D000426:Alcohol Dehydrogenase / Q000737:chemistry / Q000378:metabolism*; D000447:Aldehydes / Q000737:chemistry*; D000818:Animals; D055162:Biocatalysis; D006736:Horses; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D008099:Liver / Q000201:enzymology*; D015394:Molecular Structure; D020005:Propanols / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D020005:Propanols; D000426:Alcohol Dehydrogenase