Insights into the effect of imidazolium-based ionic liquids on chemical structure and hydrolytic activity of microbial lipase

Nascimento, Paloma Andrade Martins; Pereira, Jorge Fernando Brandão; Santos-Ebinuma, Valéria de Carvalho

doi:10.1007/s00449-019-02121-w

Cited by 11 publications

(15 citation statements)

References 58 publications

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“…On the other hand, the use of more hydrophilic 1-ethyl-3-methyl imidazolium (EMIM) cation has been recommended for BTL2 [116]. Similarly, for other lipases it has been also shown how the shorter the alkyl chain in the cationic imidazolium, the higher the activity [119], while Filice et al recommended the use of hexafluorophosphate (PF 6 -) combined with EMIM [116]. In fact, by looking at the progress curves obtained in the ethanolysis of (R,S)-1 using EtOH/EMIMPF 6 and depicted in Figure 5a (90 • C) and Figure 5b (120 • C), the kinetic resolutions are quite good, although better at 90 • C. In any case, it is noteworthy to observe how BTL2 is totally enantioselective under these reaction conditions, as no traces of the "canonical" (R)-2 isomer were detected.…”

Section: Discussionmentioning

confidence: 99%

Biocatalysis at Extreme Temperatures: Enantioselective Synthesis of both Enantiomers of Mandelic Acid by Transesterification Catalyzed by a Thermophilic Lipase in Ionic Liquids at 120 °C

Ramos-Martín¹,

Khiari²,

Alcántara³

et al. 2020

Catalysts

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The use of biocatalysts in organic chemistry for catalyzing chemo-, regio- and stereoselective transformations has become an usual tool in the last years, both at lab and industrial scale. This is not only because of their exquisite precision, but also due to the inherent increase in the process sustainability. Nevertheless, most of the interesting industrial reactions involve water-insoluble substrates, so the use of (generally not green) organic solvents is generally required. Although lipases are capable of maintaining their catalytic precision working in those solvents, reactions are usually very slow and consequently not very appropriate for industrial purposes. Increasing reaction temperature would accelerate the reaction rate, but this should require the use of lipases from thermophiles, which tend to be more enantioselective at lower temperatures, as they are more rigid than those from mesophiles. Therefore, the ideal scenario would require a thermophilic lipase capable of retaining high enantioselectivity at high temperatures. In this paper, we describe the use of lipase from Geobacillus thermocatenolatus as catalyst in the ethanolysis of racemic 2-(butyryloxy)-2-phenylacetic to furnish both enantiomers of mandelic acid, an useful intermediate in the synthesis of many drugs and active products. The catalytic performance at high temperature in a conventional organic solvent (isooctane) and four imidazolium-based ionic liquids was assessed. The best results were obtained using 1-ethyl-3-methyl imidazolium tetrafluoroborate (EMIMBF4) and 1-ethyl-3-methyl imidazolium hexafluorophosphate (EMIMPF6) at temperatures as high as 120 °C, observing in both cases very fast and enantioselective kinetic resolutions, respectively leading exclusively to the (S) or to the (R)-enantiomer of mandelic acid, depending on the anion component of the ionic liquid.

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Section: Discussionmentioning

confidence: 99%

Biocatalysis at Extreme Temperatures: Enantioselective Synthesis of both Enantiomers of Mandelic Acid by Transesterification Catalyzed by a Thermophilic Lipase in Ionic Liquids at 120 °C

Ramos-Martín¹,

Khiari²,

Alcántara³

et al. 2020

Catalysts

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show abstract

“…On the other hand, the use of more hydrophilic 1-ethyl-3-methyl imidazolium (EMIM) cation has been recommended for BTL2 [140]. Similarly, for other lipases it has been also shown how the shorter the alkyl chain in the cationic imidazolium, the higher the activity [143], while Filice et al…”

Section: Discussionmentioning

confidence: 99%

Biocatalysis at Extreme Temperatures: Enantioselective Synthesis of both Enantiomers of Mandelic Acid by Transterification Catalyzed by a Thermophilic Lipase in Ionic Liquids at 120 °C

Ramos-Martín¹,

Khiari²,

Alcántara³

et al. 2020

Preprint

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“…Researchers have used ILs as additives or reaction media for whole-cell processes, solvents, or cosolvents in such systems [18]. For instance, Aspergillus niger lipase showed enhanced activity in ILs with a short cation alkyl side chain length, namely, 1-butylimidazolium chloride, [bmim]Cl, and 1-hexyl-3-methylimidazolium chloride, [hmim]Cl [19]. Researchers have tested commercial proteases (Neutrase 0.8 L, Flavourzyme 500 L, and Alcalase 2.4 L) with the ILs choline chloride, tetramethylammonium bromide, and [emim]Br and observed a 20%, 15%, and 150% increase in protease activity, respectively, with respect to control samples [20].…”

Section: Enzyme Stabilization In Ilsmentioning

confidence: 99%

Facilitating enzymatic reactions by using ionic liquids: A mini review

Elgharbawy

Moniruzzaman

Goto

2021

Current Opinion in Green and Sustainable Chemistry

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Over the past two decades, ionic liquids (ILs) have been widely used for enzymatic conversions of substratesespecially substrates that are insoluble in common organic solvents and waterresulting in high conversion rates, high selectivity, and improved enzyme stability, wherein the ILs are recoverable and recyclable. Compared with performance in first-generation ILs, researchers recently considerably improved the technological utility of enzymes in second-and third-generation ILs composed of enzyme-benign cations and anions. Use of upgraded ILs with enzymes offers further improved activity and stability compared with research studies in the past decade, rendering IL-assisted biocatalytic processes more environmentally and economically attractive. This short review briefly presents recent developments of enzymatic reactions in ILs. The review covers approaches for and modifications of enzymes and ILs within the past 2 years for improved enzymes performance in ILs.

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Insights into the effect of imidazolium-based ionic liquids on chemical structure and hydrolytic activity of microbial lipase

Cited by 11 publications

References 58 publications

Biocatalysis at Extreme Temperatures: Enantioselective Synthesis of both Enantiomers of Mandelic Acid by Transesterification Catalyzed by a Thermophilic Lipase in Ionic Liquids at 120 °C

Biocatalysis at Extreme Temperatures: Enantioselective Synthesis of both Enantiomers of Mandelic Acid by Transesterification Catalyzed by a Thermophilic Lipase in Ionic Liquids at 120 °C

Biocatalysis at Extreme Temperatures: Enantioselective Synthesis of both Enantiomers of Mandelic Acid by Transterification Catalyzed by a Thermophilic Lipase in Ionic Liquids at 120 °C

Facilitating enzymatic reactions by using ionic liquids: A mini review

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