Bioenzymatic and Chemical Derivatization of Renewable Fatty Acids.

ABSTRACT

In addition to our previous efforts toward bioenzymatic and chemical transformations of ricinoleic acid and oleic acid to their corresponding ,-dicarboxylic acids via their ester intermediates driven in Escherichiacoli cells, several efficient oxidation conditions were investigated and optimized for the conversion of -hydroxycarboxylic acids to ,-dicarboxylic acids. Pd/C-catalyzed oxidation using NaBH4 in a basic aqueous alcohol and Ni(II) salt-catalyzed oxidation using aqueous sodium hypochlorite were considered to be excellent as a hybrid reaction for three successive chemical reactions (hydrogenation, hydrolysis, and oxidation) and an eco-friendly, cost-effective, and practical approach, respectively. Omega-hydroxycarboxylic acids and -aminocarboxylic acid were also easily prepared as useful building blocks for plastics or bioactive compounds from the bioenzymatically driven ester intermediate. The scope of the developed synthetic methods can be utilized for large-scale synthesis and various derivatizations.