Optimization of lipase-catalyzed enantioselective esterification of (±)-menthol in ionic liquid

Zhang, Dong‐Hao; Bai, Shu; Ren, Meng-Yuan; Sun, Yan

doi:10.1016/j.foodchem.2007.12.020

Cited by 52 publications

(30 citation statements)

References 23 publications

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“…Therefore, it might suggest that temperature is not very crucial for such a reaction system. However, it is important to point out that too high a temperature would cause the loss of enzyme activity [23,24].…”

Section: Effect Of Reaction Temperaturementioning

confidence: 99%

Kinetic biosynthesis of l-ascorbyl acetate by immobilized Thermomyces lanuginosus lipase (Lipozyme TLIM)

Zhang

Zhi

et al. 2011

Bioprocess Biosyst Eng

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Thermomyces lanuginosus lipase (Lipozyme TLIM)-catalyzed esterification of L-ascorbic acid was studied. It was suggested that Lipozyme TLIM was a suitable biocatalyst for enzymatic esterification of L-ascorbic acid. Three solvents were investigated for the reaction, and acetone was found to be a suitable reaction medium. Furthermore, it was found that water activity could notably affect the conversion. Moreover, pH memory of Lipozyme TLIM lipase for catalyzing L-ascorbic acid esterification in acetone was observed and the effect of pH on the reaction was estimated. In addition, the influences of other parameters such as substrate mole ratio, enzyme loading, and reaction temperature and reusability of lipase on esterification of L-ascorbic acid were also analyzed systematically and quantitatively. Kinetic characterization of Lipozyme TLIM showed that K(m,a) and V(max) were 80.085 mM and 0.747 mM min(-1), respectively. As a result, Lipozyme TLIM-catalyzed esterification of L: -ascorbic acid gave a maximum conversion of 99%.

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Section: Effect Of Reaction Temperaturementioning

confidence: 99%

Kinetic biosynthesis of l-ascorbyl acetate by immobilized Thermomyces lanuginosus lipase (Lipozyme TLIM)

Zhang

Zhi

et al. 2011

Bioprocess Biosyst Eng

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“…The predicted values of the response from the model agreed with the observed values and could be properly applied to navigate the design space. [27,28] Mutual effects of factors on the production of geranyl propionate Effect of solvent log P and time Figure 2 shows the effect of the reaction time and solvent and their mutual interaction on the CRL-MWCNTs catalysed production of geranyl propionate at constant conditions of geraniol:propionic acid molar ratio of 3:1 and 50 C. The F-value for time versus solvent (log P) showed that the effect of time on the percentage conversion of geranyl propionate was more significant than the used solvent (log P) (Table 3). However, the interaction between both of the studied parameters was significant because of the very small P-value (<0.0003).…”

Section: Resultsmentioning

confidence: 99%

Response surface methodological approach for optimizing production of geranyl propionate catalysed by carbon nanotubes nanobioconjugates

Mohamad

Huyop

Aboul‐Enein

et al. 2015

Biotechnology & Biotechnological Equipment

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Terpene esters of short-chain fatty acids are essential oils that have big importance in food, cosmetic and pharmaceutical industries as flavours and fragrances. Geraniol and citronellol are the most important substances. Considering the everincreasing demand for such products, their enzymatic production from natural raw materials by using environmentally friendly and economically attractive processes may prove advantageous. In this contribution, we would like to present an alternative option for the production of geranyl propionate using nanobioconjugates consisting of Candida rugosa lipase adsorbed onto multi-walled carbon nanotubes (CRL-MWCNTs). We investigated the effects of incubation time, temperature, solvent log P and substrate molar ratio, and determined the optimum conditions. The yield of geranyl propionate catalysed by CRL-MWCNTs nanobioconjugates was significantly influenced by two factors, namely, temperature and time of the reaction. Under the optimum reaction conditions of 55 C, solvent n-heptane (log P D 4.0), geraniol to propionic acid molar ratio of 5:1 and reaction time of 6 h, the use of CRL-MWCNTs resulted in 51.3% production of geranyl propionate. Therefore, the investigation revealed that geranyl propionate was successfully synthesized under mild conditions with reasonably high yield within a short period of time. The CRL-MWCNTs nanobioconjugates demonstrated a potential as economical and environmentally smarter biocatalysts for the production of geranyl propionate.

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“…This difference in (S)-ibuprofen yields could be attributed to the fact that ILs containing [NO 3 6 ]´anions. This difference in hydrogen bond basicity and nucleophilicity could result in a change in the conformation of the enzyme, which could lead to a loss of activity [24,25]. Therefore, the EST-catalyzed synthesis of (S)-ibuprofen would occur much more effectively in enzymatic media containing ILs with weakly coordinating anions such as [BF 4 ]´, [Tf 2 N]´, and [PF 6 ]´.…”

Section: Effects Of Ilsmentioning

confidence: 99%

Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as Cosolvent

et al. 2016

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Abstract:The aim of this study was to develop an ionic liquid (IL) system for the enzymatic resolution of racemic ibuprofen ethyl ester to produce (S)-ibuprofen. Nineteen ILs were selected for use in buffer systems to investigate the effects of ILs as cosolvents for the production of (S)-ibuprofen using thermostable esterase (EST10) from Thermotoga maritima. Analysis of the catalytic efficiency and conformation of EST10 showed that [OmPy] [BF 4 ] was the best medium for the EST10-catalyzed production of (S)-ibuprofen. The maximum degree of conversion degree (47.4%), enantiomeric excess of (S)-ibuprofen (96.6%) and enantiomeric ratio of EST10 (177.0) were achieved with an EST10 concentration of 15 mg/mL, racemic ibuprofen ethyl ester concentration of 150 mM, at 75˝C , with a reaction time of 10 h. The reaction time needed to achieve the highest yield of (S)-ibuprofen was decreased from 24 h to 10 h. These results are relevant to the proposed application of ILs as solvents for the EST10-catalyzed production of (S)-ibuprofen.

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Optimization of lipase-catalyzed enantioselective esterification of (±)-menthol in ionic liquid

Cited by 52 publications

References 23 publications

Kinetic biosynthesis of l-ascorbyl acetate by immobilized Thermomyces lanuginosus lipase (Lipozyme TLIM)

Kinetic biosynthesis of l-ascorbyl acetate by immobilized Thermomyces lanuginosus lipase (Lipozyme TLIM)

Response surface methodological approach for optimizing production of geranyl propionate catalysed by carbon nanotubes nanobioconjugates

Enzymatic Hydrolytic Resolution of Racemic Ibuprofen Ethyl Ester Using an Ionic Liquid as Cosolvent

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