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Resolution of 2-octanol via Lipase-catalyzed Enantioselective Acetylation in Organic Solvents

Chemical Research in Chinese Universities 2004年第5期20卷 575-578页

作者： WANGZhi LIZheng-qiang YuDa-hai WENGLiang LIUMing ZHANGGui-rong CAOShu-gui KeyLaboratoryforMolecularEnzymologyandEngineeringofEducationalMinistry JilinUniversityChangchun130023P.R.China LifeScienceandTechnologyInstituteofJilinUniversity Changchun130023P.R.China

The lipases from different sources were screened for their ability to catalyze the resolution of 2-octanol in organic solvents with vinyl acetate as the acylating reagent. The medium effect has been studied on the irreversible transesterification with varying water activity(a_w). The influence of vinyl acetate concentration on it has also been investigated. Under the optimal conditions, the enantiomeric ratio(E value) of pseudomonas fluorescence lipase(PFL) exceeded 200 with an enantiomeric excess(e.e.) of S-2-octanol above 99% at a 51% degree of conversion.

关键词： Lipase Resolution Activity Enantioselectivity 2-octanol

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Optimization and kinetic modeling of lipase mediated enantioselective kinetic resolution of (±)-2-octanol

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Natural Science 2013年第9期5卷 1025-1033页

作者： Jyoti B. Sontakke Ganapati D. Yadav Department of Chemical Engineering Institute of Chemical Technology Mumbai India

Chiral 2-octanol is one of the key intermediates for preparation of liquid crystal materials, as well as many optically active pharmaceuticals. Lipase catalyzed kinetic resolution has proved to be an efficient technique for synthesis of enantiomerically enriched compounds. In the present study, optimization and kinetic modeling of kinetic resolution of (±)-2-octanol was done by using vinyl acetate as an acyl donor in n-heptane as a solvent. Response surface methodology (RSM) and four-factor-five-level Centre Composite Rotatable Design (CCRD) were employed to evaluate the effect of various parameters such as speed of agitation, enzyme loading, temperature and acyl donor/alcohol molar ratio on conversion, enantiomeric excess (ee), enantioselectivity and initial rate of reaction. Acylation of 2-octanol with vinyl acetate catalyzed by Novozyme 435 follows the ternary complex mechanism (ordered bi-bi mechanism) with inhibition by 2-octanol.

关键词： Immobilized Lipase Novozyme 435 2-octanol Response Surface Methodology Kinetic Modeling Enantioselectivity

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