Surfactant‐Coated Lipase Suitable for the Enzymatic Resolution of Menthol as a Biocatalyst in Organic Media

Abstract

Enantioselective esterification of menthol with fatty acids using a surfactant‐coated lipase was carried out in organic media. The surfactant‐coated lipase originating from Candida cylindracea appeared to be highly enantioselective and good biocatalyst for the resolution of racemic menthol. The enzymatic activity of the lipase in organic media was significantly increased by a coating with a nonionic surfactant. The reaction rate of the coated lipase was more than 100 times that of the powder lipase. In order to investigate the effect of the organic solvent on enantioselectivity, 19 kinds of solvents were employed. The nature of the organic solvent strongly affected the efficiency of the biocatalyst and the enantioselectivity. Among them, isooctane was the best organic solvent from the viewpoint of reaction rate and enantioselectivity. The effect of reaction temperature on esterification was also investigated. The optimal reaction temperature was around 35 °C. The enzymatic activities using n‐saturated fatty acids with different alkyl chain lengths were compared, and long‐chain fatty acids were found to be better substrates than shorter ones. The relationship between the initial rate of the esterification and the carbon number of the fatty acid was not linear. These results suggest that there are inherent Km values for each fatty acid.

Stereoselective acylation of Dl‐menthol in organic solvents by an immobilized lipase from Pseudomonas cepacia with vinyl propionate

“…At 30°C, nearly 50% of (−)-menthol was converted to the ester form after 48 h incubation. The reaction rate was comparable to enzymatic resolutions of (±)-menthol obtained previously with lipase from C. cylindracea (1,12).…”

“…In recent years, the use of lipases as biocatalysts for enzymatic resolution of racemic substances has increasingly attracted research interest because of their demonstrated high enantioselectivity compared to chemical catalysts (1). In addition, lipases are readily available, relatively inexpensive, and have no cofactor requirement (2).…”

Sustainable production of the emulsifier methyl oleate by Candida rugosa lipase nanoconjugates

“…nonionic, cationic, anionic and zwitterionic), surfactants are useful for modulating certain interactions. Therefore, the effect of surfactant on lipase interactions would depend strongly on the choice of both lipase and surfactant included in the reactions (Kamiya et al, 1995). It was observed that after 11 h of reaction, the Triton X-100 (non-ionic) yielded the highest percentage of acid conversion for CRL-MWCNTs (to 83.62%) when compared with that of free…”

A thermodynamic study of the ketoreductase-catalyzed reduction of 2-alkanones in non-aqueous solvents

“…Lipase-catalyzed esterification [4][5][6] and transesterification [1,7] reactions in organic solvents have been commonly used for the enantioselective resolution of racemic mixtures. Recently, ketoreductase-catalyzed reactions [8][9][10][11][12] have been used for the production of chiral secondary alcohols from the corresponding ketones.…”