Laccase-Mediator System for Alcohol Oxidation to Carbonyls or Carboxylic Acids: Toward a Sustainable Synthesis of Profens

• Published in: ChemSusChem Vol. 7; no. 9; pp. 2684 - 2689
• Main Authors: Galletti, Paola, Pori, Matteo, Funiciello, Federica, Soldati, Roberto, Ballardini, Alberto, Giacomini, Daria
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.09.2014; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: Acids; Alcohol; alcohols; Alcohols - chemistry; Aldehydes - chemistry; Carboxylic Acids - chemistry; Chemistry Techniques, Synthetic; drug design; enzyme catalysis; Free radicals; Green Chemistry Technology; Ketones - chemistry; Laccase - metabolism; Oxidation; Oxidation-Reduction; Propionates - chemical synthesis; Propionates - chemistry; selectivity; Stereoisomerism; Substrate Specificity; Trametes - enzymology; Trametes versicolor; selectivity; oxidation; enzyme catalysis; alcohols; drug design
• ISSN: 1864-5631; 1864-564X
• DOI: 10.1002/cssc.201402136

By combining two green and efficient catalysts, such as the commercially available enzyme laccase from Trametes versicolor and the stable free radical 2,2,6,6‐tetramethylpiperidine‐N‐oxyl (TEMPO), the oxidation in water of some primary alcohols to the corresponding carboxylic acids or aldehydes and of selected secondary alcohols to ketones can be accomplished. The range of applicability of bio‐oxidation is widened by applying the optimized protocol to the oxidation of enantiomerically pure 2‐arylpropanols (profenols) into the corresponding 2‐arylpropionic acids (profens), in high yields and with complete retention of configuration. Enzyme exploitation: Laccase from Trametes versicolor (TvL) is used in a chemoenzymatic system with 2,2,6,6‐tetramethylpiperidine‐N‐oxyl (TEMPO) in water for the environmentally friendly oxidation of primary alcohols into the corresponding carboxylic acids or aldehydes and of selected secondary alcohols to ketones.