title: Chemoenzymatic synthesis of (2S)-2-arylpropanols through a dynamic kinetic resolution of 2-arylpropanals with alcohol dehydrogenases.
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.
authors.affiliation: Department of Chemistry G. Ciamician, University of Bologna, Via Selmi 2, Bologna, I-40126, Italy. paola.galletti@unibo.it
authors.forename: Paola
authors.initials: P
authors.lastname: Galletti
authors.forename: Enrico
authors.initials: E
authors.lastname: Emer
authors.forename: Gabriele
authors.initials: G
authors.lastname: Gucciardo
authors.forename: Arianna
authors.initials: A
authors.lastname: Quintavalla
authors.forename: Matteo
authors.initials: M
authors.lastname: Pori
authors.forename: Daria
authors.initials: D
authors.lastname: Giacomini
mesh_terms: 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
chemical_list: D000447:Aldehydes; D020005:Propanols; D000426:Alcohol Dehydrogenase