Synthesis of acyclic quaternary ammonium compounds containing ω-alkoxyethyl and 2-hydroxyethyl substituents at the nitrogen atom

Tcarkova, K. V.; Belus, S. K.; Аrtyushin, О. I.; Харламов, А. В.; Бондаренко, Н. А.

doi:10.1007/s11172-015-1209-7

Cited by 3 publications

(3 citation statements)

References 5 publications

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“…The synthesis of ILs was described in previous studies 20‐22 . Briefly, 0.05 mol of 1‐chlorooctane was added to a 33% (v/v) dimethylamine aqueous solution using a drop funnel.…”

Section: Methodsmentioning

confidence: 99%

“…The synthesis of ILs was described in previous studies. [20][21][22] Briefly, 0.05 mol of 1-chlorooctane was added to a 33% (v/v) dimethylamine aqueous solution using a drop funnel. The reaction was maintained for 2 h in an ice bath, then heated under reflux at 80 °C for 30 h. The reaction solution was then cooled to room temperature and washed.…”

Section: Synthesis Of Ionic Liquid Modifiersmentioning

confidence: 99%

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Ionic liquid modification reshapes the substrate pockets of lipase to boost its stability and activity in vitamin E succinate synthesis

Ma,

Zhang,

Chen

et al. 2023

J Sci Food Agric

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BACKGROUNDThe relative low stability, reusability and activity of enzymes made the industrial production of vitamin E succinate (VES) can only be performed with complex processes and high cost using chemical methods. To address these issues, in the present study, an ionic liquids (ILs) modification strategy was developed to improve the activity and stability of lipases in VES synthesis.RESULTSThe results showed that the [1‐butyl‐3‐methyl imidazole] [N‐acetyl‐l‐proline] ILs modified Candida rugosa lipase (CRL) has the highest modification degree (48.28%), activity (774 U g−1), thermostability and solvent tolerance in three selected modifiers. Additionally, after reaction condition optimization, the highest yield of VES can be improved to 95.18% at 45 °C for 15 h, which was significantly improved compared to some previous studies.CONCLUSIONIn the present study, a high‐efficiency VES synthesis strategy was successfully developed via modification of lipase. Moreover, the mechanism by which ILs modification can enhance the activity and stability of lipase was investigated via both experimental and computational‐aided methods. Molecular dynamics simulation suggested that ILs modification changed the geometry of Phe344 from flat to upright, which significantly reshaped and enhanced the size of substrate binding pocket of CRL. It is also agreement with our circular dichroism and fluorescence spectroscopy results, which suggested that the modification changed the secondary structure of CRL to a certain extent. The larger pocket also endowed the suitable binding pose of succinate, which made the hydrogen bonds between succinate and active site Ser209 become stronger, and thus improving the yield of VES. © 2023 Society of Chemical Industry.

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“…The synthesis of ILs was described in previous studies 20‐22 . Briefly, 0.05 mol of 1‐chlorooctane was added to a 33% (v/v) dimethylamine aqueous solution using a drop funnel.…”

Section: Methodsmentioning

confidence: 99%

Section: Synthesis Of Ionic Liquid Modifiersmentioning

confidence: 99%

Ionic liquid modification reshapes the substrate pockets of lipase to boost its stability and activity in vitamin E succinate synthesis

Ma,

Zhang,

Chen

et al. 2023

J Sci Food Agric

View full text Add to dashboard Cite

show abstract

“…The synthesis of ionic liquids was referred to previous reports ( Li et al, 2012 ; Kharlamov et al, 2014 ; Tcarkova et al, 2015 ). 0.01 mol of chlorobutane (chlorooctane, chlorododecane, chlorohexadecane) was added to a 33% (v/v) dimethylamine aqueous solution using a constant pressure drop funnel and the reaction was maintained for 1 h in an ice bath, then heated under reflux at 50–100°C for 24 h. The reaction solution was then cooled to room temperature and washed three times with distilled water to obtain a yellow oily liquid.…”

Section: Methodsmentioning

confidence: 99%

Enhancing the Catalytic Performance of Candida antarctica Lipase B by Chemical Modification With Alkylated Betaine Ionic Liquids

Xue

Zhang

et al. 2022

Front. Bioeng. Biotechnol.

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Various betaine ionic liquids composed of different chain lengths and different anions were designed and synthesized to modify Candida antarctica lipase B (CALB). The results showed that the catalytic activity of all modified lipases improved under different temperature and pH conditions, while also exhibiting enhanced thermostability and tolerance to organic solvents. With an increase in ionic liquid chain length, the modification effect was greater. Overall, CALB modified by [BetaineC16][H2PO4] performed best, with the modified CALB enzyme activity increased 3-fold, thermal stability increased 1.5-fold when stored at 70°C for 30 min, with tolerance increased 2.9-fold in 50% DMSO and 2.3-fold in 30% mercaptoethanol. Fluorescence and circular dichroism (CD) spectroscopic analysis showed that the introduction of an ionic liquid caused changes in the microenvironment surrounding some fluorescent groups and the secondary structure of the CALB enzyme protein. In order to establish the enzyme activity and stability change mechanisms of the modified CALB, the structures of CALB modified with [BetaineC4][Cl] and [BetaineC16][Cl] were constructed, while the reaction mechanisms were studied by molecular dynamics simulations. Results showed that the root mean square deviation (RMSD) and total energy of modified CALB were less than those of native CALB, indicating that modified CALB has a more stable structure. Root mean square fluctuation (RMSF) calculations showed that the rigidity of modified CALB was enhanced. Solvent accessibility area (SASA) calculations exhibited that both the hydrophilicity and hydrophobicity of the modified enzyme-proteins were improved. The increase in radial distribution function (RDF) of water molecules confirmed that the number of water molecules around the active sites also increased. Therefore, modified CALB has enhanced structural stability and higher hydrolytic activity.

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Structures and NMR spectra of N-(ω-alkoxyethyl)N-(2-hydroxyethyl)-N, N-dimethylammonium chlorides

et al. 2015

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Synthesis of acyclic quaternary ammonium compounds containing ω-alkoxyethyl and 2-hydroxyethyl substituents at the nitrogen atom

Cited by 3 publications

References 5 publications

Ionic liquid modification reshapes the substrate pockets of lipase to boost its stability and activity in vitamin E succinate synthesis

Ionic liquid modification reshapes the substrate pockets of lipase to boost its stability and activity in vitamin E succinate synthesis

Enhancing the Catalytic Performance of Candida antarctica Lipase B by Chemical Modification With Alkylated Betaine Ionic Liquids

Structures and NMR spectra of N-(ω-alkoxyethyl)N-(2-hydroxyethyl)-N, N-dimethylammonium chlorides

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