Lipase-catalyzed dynamic kinetic resolution of racemic ibuprofen ester via hollow fiber membrane reactor: Modeling and simulation

Lau, Sie Yon; Uzir, Mohamad Hekarl; Kamaruddin, Azlina Harun; Bhatia, Subhash

doi:10.1016/j.memsci.2010.04.008

Cited by 20 publications

(32 citation statements)

References 22 publications

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“…The substrate ((S)-ibuprofen ester) and the by-product (alcohol) were found to be uncompetitive and competitive inhibitors, respectively (Lau 2013;Sie Yon et al 2013). The reaction mechanism of the enzyme-catalyzed conversion of substrate (S) to product (P 0 ) is clearly illustrated in Fig.…”

Section: Enzymatic Hydrolysis and Racemizationmentioning

confidence: 97%

“…The DEKR process has been proposed to take place in a membrane-mediated reactor (Wang et al 2004;Lau et al 2010Lau et al , 2011. The reactor is divided into two compartments by a semi-permeable membrane.…”

Section: In-situ Dekr In Hollow-fiber Membrane Reactormentioning

confidence: 99%

“…The reaction media in the enzymatic membrane reactor (EMR) can be of aqueous, organic and two-liquid phases (organic-aqueous). The versatility of the two-liquid phases in hollow-fiber membrane reactor for DEKR for the production of (S)-ibuprofen acid has been investigated (Sie Yon et al 2013;Lau et al 2010). Polyacrylonitrile (PAN) has been used as membrane material due to its superior resistance to hydrolysis and oxidation.…”

Section: In-situ Dekr In Hollow-fiber Membrane Reactormentioning

confidence: 99%

“…The cross-section of an asymmetric hollow fiber membrane is illustrated in Fig. 16.17 (Lau et al 2010). In the diffusion layer, the racemization of the unreacted substrate takes place spontaneously by the base-catalyzed reaction.…”

Section: Process Modelling Of Dekr In Membrane Reactormentioning

confidence: 99%

“…The derivation of the mechanism is based on a rapid equilibrium assumption in which the rates of formation and dissociation of the enzyme-substrate complexes (denoted as ES, ES*, ESS*, EI or ESI) reach the equilibrium state instantly compared to that of the rate formation of the free enzyme (denoted as E) and product. The reaction rate of the EKR process for both (R)-and (S)-enantiomers is represented by the following kinetic model (Lau et al 2010;Lau 2013); Fig. 16.18 Kinetic mechanism of enzymatic hydrolysis of racemic ibuprofen ester with uncompetitive substrate inhibition and non-competitive product inhibition.…”

Section: Enzymatic Hydrolysis and Racemizationmentioning

confidence: 99%

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Advances in Bioprocess Technology

Ravindra¹

2015

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Section: Enzymatic Hydrolysis and Racemizationmentioning

confidence: 97%

Section: In-situ Dekr In Hollow-fiber Membrane Reactormentioning

confidence: 99%

Section: In-situ Dekr In Hollow-fiber Membrane Reactormentioning

confidence: 99%

Section: Process Modelling Of Dekr In Membrane Reactormentioning

confidence: 99%

Section: Enzymatic Hydrolysis and Racemizationmentioning

confidence: 99%

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Advances in Bioprocess Technology

Ravindra¹

2015

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Factors screening to statistical experimental design of racemic atenolol kinetic resolution via transesterification reaction in organic solvent using free Pseudomonas fluorescens lipase

2017

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As the (R)‐enantiomer of racemic atenolol has no β‐blocking activity and no lack of side effects, switching from the racemate to the (S)‐atenolol is more favorable. Transesterification of racemic atenolol using free enzymes investigated as a resource to resolve the racemate via this method is limited. Screenings of enzyme, medium, and acetyl donor were conducted first to give Pseudomonas fluorescens lipase, tetrahydrofuran, and vinyl acetate. A statistical design of the experiment was then developed using Central Composite Design on some operational factors, which resulted in the conversions of 11.70–61.91% and substrate enantiomeric excess (ee) of 7.31–100%. The quadratic models are acceptable with R2 of 95.13% (conversion) and 89.63% (ee). The predicted values match the observed values reasonably well. Temperature, agitation speed, and substrate molar ratio factor have low effects on conversion and ee, but enzyme loading affects the responses highly. The interaction of temperature–agitation speed and temperature–substrate molar ratio show significant effects on conversion, while temperature–agitation speed, temperature–substrate molar ratio, and agitation speed–substrate molar ratio affect ee highly. Optimum conditions for the use of Pseudomonas fluorescens lipase, tetrahydrofuran, and vinyl acetate were found at 45°C, 175 rpm, 2000 U, and 1:3.6 substrate molar ratio.

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Influence of the Reactor Configuration on the Enantioselectivity of a Kinetic Resolution

Liese

Kragl

2013

Chemie Ingenieur Technik

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Die optische Reinheit eines Produkts am Reaktorausgang hängt nicht nur von der Enantioselektivität des Katalysators ab, sondern auch von der Reaktorkonfiguration. Für die kinetische Racematspaltung werden verschiedene Reaktortypen in Hinblick auf den erzielbaren Enantiomerenüberschuss (ee) bei einem bestimmten Umsatz verglichen. Während für den kontinuierlich betriebenen Rührkesselreaktor ein hoher ee nur bei Enantioselektivitäten (E‐Werte) von größer 190 erhalten wird, gelingt dies unter Batch‐, Fed‐batch‐ und Strömungsrohrbedingungen schon bei E‐Werten von 35.

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Lipase-catalyzed dynamic kinetic resolution of racemic ibuprofen ester via hollow fiber membrane reactor: Modeling and simulation

Cited by 20 publications

References 22 publications

Advances in Bioprocess Technology

Advances in Bioprocess Technology

Factors screening to statistical experimental design of racemic atenolol kinetic resolution via transesterification reaction in organic solvent using free Pseudomonas fluorescens lipase

Influence of the Reactor Configuration on the Enantioselectivity of a Kinetic Resolution

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