Stereoselective enzymatic reduction of 1,4-diaryl-1,4-diones to the corresponding diols employing alcohol dehydrogenases

Due to the steric hindrance of the starting prochiral ketones, the preparation of chiral 1,4-diaryl-1,4-diols through the asymmetric hydrogen transfer reaction has been mainly restricted to the use of metal-based catalysts, oxazaborolidines, or organocatalysts. Herein, we demonstrated the versatility of oxidoreductases, finding overexpressed alcohol dehydrogenase from Ralstonia sp. (E. coli/RasADH) as the most active and stereoselective biocatalyst. Thus, the preparation of a set of 1,4-diaryl-1,4-diols bearing different pattern substitutions in the aromatic ring was achieved with complete diastereo- and enantioselectivity under mild reaction conditions.Ministerio de Economía y Competitividad CTQ2016-75752-

Broadening the Chemical Scope of Laccases: Selective Deprotection of N-Benzyl Groups

El sistema catalítico formado por la lacasa de Trametes versicolor y el TEMPO es utilizado de forma eficiente para llevar a cabo la desprotección quimioselectiva de los grupos N-bencilo primarios en condiciones suaves de reacción.Laccase from Trametes versicolor together with TEMPO has been found as a very efficient system to deprotect Nbenzylated primary amines, differing from previously described methods since it uses oxygen as mild oxidant in aqueous medium. Chemoselective removal of the benzyl group was achieved with excellent yields when secondary amine and alcohol moieties were also presentMICINN (Projects CTQ2011-24237 and CTQ2013-44153). Principado de Asturias (predoctoral fellowship Severo Ochoa)