Reaction of esterase of Pseudomonas sp. NOF-5 on terpene alcohols and esters. Part IV. Enantioselective esterification of racemic terpene alcohols with fatty acids by Pseudomonas sp. NOF-5 strain.

Abstract

The microbial esterification of (±)-menthol with various fatty acids by Pseudomonas sp. NOF-5 strain was investigated. A water insoluble fatty acid higher than caproic acid was esterified with (-)-menthol with high enantioselectivity; especially, when lauric acid was used as the fatty acid, the yield of ester was satisfactory. The microbial esterification of various racemic terpene alcohols with lauric acid by the same microorganism was further studied. (-)-Isopulegol and (-)-trans-carveol were esterified from their racemates with high stereoselectivity. However, the esterification of (±)-cis-carveol was with poor enantioselectivity, and (±)-citronellol was entirely nonselective.