Soybean (Glycine max) as a versatile biocatalyst for organic synthesis

Abstract

A series of aliphatic and aromatic aldehydes and ketones were reduced using plant cell preparations of Glycine max seeds (soybean). The biotransformation of five aromatic aldehydes in water, at room temperature afforded the corresponding alcohols in excellent yields varying from 89 to 100%. Two prochiral aromatic ketones yielded the alcohol in very low conversion, 1% and to 4%; however with good enantiomeric excess (ee) of 99 and 79%, respectively. Additionally, three prochiral and one cyclic aliphatic ketones produced the corresponding alcohols in moderate yields varying from 10 to 58% and ee varying from 73 to 99%. Hydrolysis of two aromatic esters yielded the expected carboxylic acids in 49 and 66%. Most of the obtained alcohols have commercial value as cosmetic fragrances. Although, the enzymes present in soybean (reductase/lipase) has not been defined, the reaction is an important route for the preparation of pure alcohols and carboxylic acid, with low cost and environmental impact.

Keywords: Glycine max, biocatalysis, bioreduction, aldehydes and ketones, ester hydrolysis