Improved activity and stability of <i>pseudomonas capaci</i> lipase in a novel biocompatible ionic liquid, 1‐isobutyl‐3‐methylimidazolium hexafluorophosphate

Shan, Hongyan; Li, Zaijun; Li, Ming; Ren, Guoxia; Fang, Yinchun

doi:10.1002/jctb.1887

Cited by 36 publications

(18 citation statements)

References 29 publications

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“…[16][17][18][19] AAILs have been employed as chiral solvents or reactants for dissolution and stabilization of cellulose, nucleic acids, carbohydrates and other species of primary biological importance. [20][21][22][23][24][25] On the theoretical front, molecular dynamics (MD) simulations on the ILs composed of deprotonated amino acid anions and choline cation revealed that their formation is facilitated through proton transfer involving the hydrogen bond effectively neutralizing cation and anion. 26 Fileti and coworkers 27 A molecular level understanding of noncovalent interactions encompassing hydrogen bonding, steric repulsion, aromatic ring stacking and electrostatic interactions should prove useful 5 for designing of task specific ILs.…”

Section: Introductionmentioning

confidence: 99%

Electronic Structure, NMR, Spin–Spin Coupling, and Noncovalent Interactions in Aromatic Amino Acid Based Ionic Liquids

Rao

Gejji

2016

J. Phys. Chem. A

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Noncovalent interactions accompanying phenylalanine (Phe), tryptophan (Trp), and tyrosine (Tyr) amino acids based ionic liquids (AAILs) composed of 1-methyl-3-butyl-imidazole and its methyl-substituted derivative as cations have been analyzed employing the dispersion corrected density functional theory. It has been shown that cation-anion binding in these bioionic ILs is primarily facilitated through hydrogen bonding in addition to lp---π and CH---π interactions those arising from aromatic moieties which can be probed through (1)H and (13)C NMR spectra calculated from the gauge independent atomic orbital method. Characteristic NMR spin-spin coupling constants across hydrogen bonds of ion pair structures viz., Fermi contact, spin-orbit and spin-dipole terms show strong dependence on mutual orientation of cation with the amino acid anion. The spin-spin coupling mechanism transmits spin polarization via electric field effect originating from lp---π interactions whereas the electron delocalization from lone pair on the carbonyl oxygen to antibonding C-H orbital is facilitated by hydrogen bonding. It has been demonstrated that indirect spin-spin coupling constants across the hydrogen bonds correlate linearly with hydrogen bond distances. The binding energies and dissected nucleus independent chemical shifts (NICS) document mutual reduction of aromaticity of hydrogen bonded ion pairs consequent to localization of π-character. Moreover the nature and type of such noncovalent interactions governing the in-plane and out-of-plane NICS components provide a measure of diatropic and paratropic currents for the aromatic rings of varying size in AAILs. Besides the direction of frequency shifts of characteristic C═O and NH stretching vibrations in the calculated vibrational spectra has been rationalized.

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Section: Introductionmentioning

confidence: 99%

Electronic Structure, NMR, Spin–Spin Coupling, and Noncovalent Interactions in Aromatic Amino Acid Based Ionic Liquids

Rao

Gejji

2016

J. Phys. Chem. A

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“…Therefore, hydrophobic ILs are used and the enzyme activity and stability is dependent on the IL. Several studies in the literature show that enzymes, majority lipases, exhibit greater stability in pure ILs than in traditional organic solvents [13,14]. A review of Zhao 2005 [15] shows that ILs with larger cations are better for enzyme activity than smaller cations.…”

Section: Lipasesmentioning

confidence: 99%

New Generations of Ionic Liquids Applied to Enzymatic Biocatalysis

Tavares¹,

Rodrı́guez²,

Macedo³

2013

Ionic Liquids - New Aspects for the Future

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dissolve nonpolar substrates, while avoiding enzyme inactivation like water-miscible organic solvents, as DMSO or acetonitrile, often do [6]. Another mentioned characteristic of ILs is the possibility of obtaining the desired physicochemical properties by selecting combinations of cations and anions ("tunability"), which makes them "designer solvents". For example, ILs can be produced to be water-miscible, partially miscible or totally immiscible, and can also be synthesized with different viscosities. These interesting properties make them a very important reaction media for enzyme stabilization and reaction. The use of organic solvents in bioprocess presents a number of further problems. The main concerns are the toxicity of the organic solvents to both the process operators and the environment (eco-toxicity), and also the volatile and flammable nature of these solvents, which make them a potential explosion hazard [7]. Thus, ILs have emerged as a potential replacement for organic solvents in biocatalytic processes at both laboratory and industrial scale. The negligible vapor pressure means that they emit no volatile compounds, and also introduces the additional possibility of removal of products by distillation without further contamination by the solvent. It also facilitates the recycling of ILs, decreasing operation costs. All these properties make ILs very important for the stabilization and activation of enzymes; therefore, numerous enzymatic reactions have been investigated in different types of ILs as will be shown in the next sections. Several topics about biocatalysis in ILs will be reviewed: their effect on the activity and stability of enzymes, toxicity of ILs, new generation of ILs and methods to stabilize enzymes will be discussed.

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“…The conformational stability of proteins is affected vastly by environmental changes such as high temperature and presence of salts [1,2]. Ionic liquids have gained importance in industrial and biotechnical processes [3][4][5][6][7][8] which is an area of considerable potential. The literature is available on thermodynamical properties of mixtures containing ionic liquids [9][10][11][12][13][14] as well as amino acids [15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Solute–solvent interactions of glycine, l -alanine, and l -valine in aqueous 1-methyl imidazolium chloride ionic liquid solutions in the temperature interval (288.15 to 308.15) K

Pal

Kumar

Maan³

et al. 2015

The Journal of Chemical Thermodynamics

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Improved activity and stability of pseudomonas capaci lipase in a novel biocompatible ionic liquid, 1‐isobutyl‐3‐methylimidazolium hexafluorophosphate

Cited by 36 publications

References 29 publications

Electronic Structure, NMR, Spin–Spin Coupling, and Noncovalent Interactions in Aromatic Amino Acid Based Ionic Liquids

Electronic Structure, NMR, Spin–Spin Coupling, and Noncovalent Interactions in Aromatic Amino Acid Based Ionic Liquids

New Generations of Ionic Liquids Applied to Enzymatic Biocatalysis

Solute–solvent interactions of glycine, l -alanine, and l -valine in aqueous 1-methyl imidazolium chloride ionic liquid solutions in the temperature interval (288.15 to 308.15) K

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