Ketone-Alcohol Hydrogen Transfer Equilibria: Is the Biooxidation of Halohydrins Blocked?

FABRICIO R. BISOGNO

CHEMISTRY-A EUROPEAN JOURNAL

WILEY-V C H VERLAG GMBH

Año: 2010

0947-6539

font size="2"> In order to ensure the quasi-irreversibility of the oxidation of alcohols coupled with the reduction of ketones in a hydrogen transfer (HT) fashion, stoichiometric amounts of £-halo carbonyl compounds as hydrogen acceptors have been employed. The reason why these substrates lead to quasi-quantitative conversions has been tacitly attributed to both thermodynamic and kinetic effects. In order to provide a clear rationale for this behavior, we study here the redox equilibrium of a selected series of ketones and 2-propanol by undertaking an approach that combines experimental and theoretical elements. First, the activity of the R-specific alcohol dehydrogenase from Lactobacillus brevis