Experimental design of the kinetic resolution of a key precursor of high-value bioactivemyo-inositols by an immobilized lipase

In this study, we use natural halloysitum rubrum as novel support materials to immobilize Candida rugosa lipase. The response surface methodology with a four-factor three-level Box-Behnken experimental design was used to evaluate the effects of immobilization parameters, such as pH (4.0 to 6.0), immobilization temperature (25 °C to 35 °C), enzyme/support ratio (0.1 to 0.3, w/w), and immobilization time (1 h to 2 h), on the activity of immobilized lipase. The optimum pH, temperature, enzyme/support ratio, and time for immobilized lipase activity (376.09 U/g) were 5.17, 29.65 °C, 0.3 (w/w), and 1.63 h, respectively. After 15 repeated uses, the immobilized lipase still retained 80% of its initial activity, which indicates good reusability.

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Dynamic Kinetic Resolution of Sec-Alcohols in Ionic Liquids/Supercritical Carbon Dioxide Biphasic Systems

International Journal of Chemical Reactor Engineering ◽

10.2202/1542-6580.2106 ◽

2009 ◽

Vol 7 (1) ◽

Cited By ~ 4

Author(s):

Pedro Lozano ◽

Teresa De Diego ◽

Michel Vaultier ◽

Jose L Iborra

Keyword(s):

Carbon Dioxide ◽

Ionic Liquids ◽

Supercritical Carbon Dioxide ◽

Kinetic Resolution ◽

Immobilized Lipase ◽

Enzymatic Catalysis ◽

Chemical Properties ◽

Dynamic Kinetic Resolution ◽

Biphasic Systems ◽

Supercritical Carbon

Supercritical fluids and ionic liquids are neoteric solvents that can be used as non-conventional reaction media for enzymatic catalysis under optimised conditions. These solvents exhibit many different physical and chemical properties, but have two cross-points: they are not-miscible and can be easily separated from substrates and products, and they can be reused. As supercritical carbon dioxide (scCO2) can dissolve in the ionic liquid (IL) phase (up to 0.7 mole fraction), a new concept of biphasic bioreactors for Fine Chemicals syntheses may be developed by using both enzyme and chemical catalysts "immobilized" into the IL phase, and substrates transported by the scCO2 phase. The system was tested for the continuous chemoenzymatic dynamic kinetic resolution (DKR) of rac-1-phenylethanol in IL/scCO2 by using simultaneously immobilized lipase (Novozym 435) and acid zeolites catalysts at 50°C and 100 bars, providing good yields (up 98.0 %) for R-phenylethyl propionate ester with excellent enantioselectivity (up to 97.3 %), and without any activity loss after 14 days of operation.

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Enhancement of the Efficiency of the Low Temperature Method for Kinetic Resolution of Primary Alcohols by Optimizing the Organic Bridges in Porous Ceramic-Immobilized Lipase.

ChemInform ◽

10.1002/chin.200343040 ◽

2003 ◽

Vol 34 (43) ◽

Author(s):

Takashi Sakai ◽

Kyoko Hayashi ◽

Fumika Yano ◽

Mie Takami ◽

Megumi Ino ◽

...

Keyword(s):

Low Temperature ◽

Kinetic Resolution ◽

Immobilized Lipase ◽

Porous Ceramic ◽

Primary Alcohols ◽

Temperature Method

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Optimization of Chiral Resolution of (+/-)-1-Phenylethanol by Statistical Methods

International Journal of Chemical Reactor Engineering ◽

10.1515/1542-6580.2656 ◽

2011 ◽

Vol 9 (1) ◽

Cited By ~ 1

Author(s):

Ganapati D. Yadav ◽

Jyoti B. Sontakke

Keyword(s):

Kinetic Resolution ◽

Batch Reactor ◽

Immobilized Lipase ◽

Enantiomeric Excess ◽

Molar Ratio ◽

Catalyst Loading ◽

Acyl Donor ◽

Reaction Conditions ◽

Optimum Reaction ◽

Synthetic Intermediate

Optically active 1-phenylethanol is used as a chiral building block and synthetic intermediate in pharmaceutical and fine-chemical industries. Lipase - catalyzed kinetic resolution of (R,S)-1-phenylethanol with vinyl acetate as an acyl donor and Candida antarctica immobilized lipase as a biocatalyst in a batch reactor was optimized using Response Surface Methodology (RSM). Four-factor-five-level central composite rotatable design (CCRD) was employed to evaluate the effect of synthesis parameters such as speed of agitation, enzyme loading, temperature and acyl donor/alcohol molar ratio, on conversion, enantiomeric excess (ee), enantioselectivity and initial rate. Optimum reaction conditions obtained were; mole ratio of acyl donor: ester of 2:1, temperature of 42.5 °C, catalyst loading of 1.6x10-3 g.cm-3 and speed of agitation of 336 rpm. Analysis of variance was performed to determine significantly affecting variables and interactions between the process parameters.

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