161275-87-2Relevant articles and documents
LIPASE CATALYZED REACTIONS AND STRATEGY FOR ALCOHOL RESOLUTION
Langrand, Georges,Baratti, Jaquess,Buono, Gerard,Triantaphylides, Christian
, p. 29 - 32 (1986)
Asymmetric hydrolysis, ester interchange and ester formation were carried out for menthol resolution with Candida cylindracea lipase.The reactions were realized under emulsified conditions with water soluble enzyme and in organic medium with an insoluble enzyme preparation.In the latter case, an enhancement of the enantioselectivity was observed.The potentialities of ester interchange and ester formation for preparative alcohol resolutions are discussed.
Thermodynamics of the lipase-catalyzed esterification of 1-dodecanoic acid with (-)-menthol in organic solvents
Tewari, Yadu B.,Schantz, Michele M.,Vanderah, David J.
, p. 641 - 647 (2007/10/03)
The thermodynamics of the lipase-catalyzed stereospecific esterification of 1-dodecanoic acid with (-)- menthol in seven organic solvents have been investigated. Equilibrium measurements were performed using hexane, heptane, cyclohexane, toluene, 2,2,4-trimethylpentane, acetonitrile, and 2-methyl-2-butanol at the temperature T = 298.15 K. The equilibrium constants have been correlated with the (octanol + water) partition coefficients and the relative permittivities of the solvents. The saturation molalities and the (hexane + water) partition coefficients of (-)-menthol, 1-dodecanoic acid, and (-)-menthyl dodecanoate have also been determined at T = 298.15 K. The equilibrium constant of the esterification reaction in aqueous media has been calculated. An important finding is that the molality of water plays an important role in determining the extent of ester formation. In acetonitrile and 2-methyl-2-butanol, which have a very high molality of water, the formation of (-)-methyl dodecanoate is considerably smaller. However, in hydrophobic solvents with lower molalities of water, the formation of (-)-methyl dodecanoate is favored in the reaction mixture. The value of the equilibrium constant varies from 3 to 26. However, the molality of (-)-methyl dodecanoate changes from 0.034 mmol kg-1 in acetonitrile to 16 mmol kg-1 in heptane. The change in product yield is a factor of ≈500 and is a striking example of the utility of organic solvents in biocatalysis.
Quantitative Analyses of Biochemical Kinetic Resolution of Enantiomers. 2. Enzyme-Catalyzed Esterification in Water-Organic Solvent Biphasic Systems
Chen, Ching-Shih,Wu, Shih-Hsiung,Girdaukas, Gary,Sih, Charles J.
, p. 2812 - 2817 (2007/10/02)
New quantitative expressions, which relate the kinetic and thermodynamic parameters that govern the stereospecificity of enzyme-catalyzed resolution of enantiomers in biphasic aqueous-organic media, have been developed.The theoretical predictions have been verified experimentally, and the technical merit of this esterification methodology has been assessed in relation to the more conventional hydrolytic procedure.
