Lipase and Metal Chloride Hydrate-Natural Deep Eutectic Solvents Synergistically Catalyze Amidation Reaction via Multiple Noncovalent Bond Interactions

Abstract

With their extreme advantages in high surface activity, bacteriostasis, and low toxicity, lipoamino acids (LAA) attracted widespread academic and industrial interests. In this study, natural deep eutectic solvents (NADESs), were adopted as a medium of enzymatic synthesis of lauroyl glycine (LG). The highest yield of 50.49 ± 1.94% was obtained in the C-Gly system. Interestingly, a synergistic effect between CALB and NADESs was found in this section. We proposed that anions play a key role in this process. To explore it, metal chloride hydrates were added into C-Gly. Fortunately, seven kinds of three-constituent NADESs (3c-NADESs) with a low viscosity were successfully formed. All of these new-design solvents were used as a medium of enzymatic of LG, and the highest yield of LG can reach 85.97 ± 1.86% after optimization. To explore the mechanism of the synergistic effect between CALB and 3c-NADESs. The results of molecular dynamics studies (MD) showed that there was no significant change of CALB in this process, which indicated that CALB may play a secondary role in the synergistic effect. In this context, we studied the molecular interaction between Mg-CGly and lauric acid, and the reaction processes were studied in depth via IRC method. The results suggested that a strong H-bond was formed between Cl– and lauric acid. This interaction may increase the electron-attracting ability of fatty acids and make them more susceptible to be attacked by amino acids and thus to increase the yield of amidation reaction of lauric acid and glycine.

Molecular Mechanism and Extraction Performance Evaluation for Separation of Methanol and n-Hexane via Ionic Liquids as Extractant

“…The main objective of our study is to accurately understand the optimal IL to meet the needs of specific separation processes through MD simulations. Researchers use quantum chemistry (QC) and MD simulations to provide the system with basic molecular insights . These calculation techniques will also be helpful to explore a new solvent, but it cannot replace the experiment.…”

“…Researchers use quantum chemistry (QC) and MD simulations to provide the system with basic molecular insights. 20 These calculation techniques will also be helpful to explore a new solvent, but it cannot replace the experiment. Stephenson et al 21 carried out molecular simulations of mixtures of water and ethanol, which contributed significantly to the understanding of hydrogen bonds in alcohols.…”

Selective and Efficient Synthesis of Pine Sterol Esters Catalyzed by Deep Eutectic Solvent

“…As one of the 12 principles of green chemistry, the utilization of renewable feedstock as a succedaneum of the petrochemical base has always been always a key strategy to make a sustainable and green chemistry process in contemporary industries [ 1 , 2 , 3 ]. Moreover, the utilization of natural starting materials as an alternative to primary resources is of growing interesting and has attracted more attention in health-related fields [ 4 ].…”

Experimental Investigation on the Correlation between the Physicochemical Properties and Catalytic Activity of Six DESs in the Kabachnik‐Fields Reaction

“…[34] Among them, organic synthesis is one of the most relevant applications. Some recent contributions of deep eutectic solvents in organic synthesis include the synthesis of carbamates and ureas from carbonates ([ChCl][ZnCl 2 ] 2 ), [35] amidation reaction (in lipase and metal chloride hydratenatural DES), [36] activation of CO 2 and epoxide and their subsequent cycloaddition (in phosphonium-based DES), [37] synthesis of 3,4 dihydropyrimidin-2(1H)-ones/thiones, [38] synthesis of aminobenzochromenes etc. [39] In this work, six DESs were introduced to explore the utility as non-conventional media and catalyst for organic transformations, especially, multicomponent reactions and to overcome many of the obstacles encountered with conventional catalysts, using the rapid synthesis of αaminophosphonates.…”

“…Among them, organic synthesis is one of the most relevant applications. Some recent contributions of deep eutectic solvents in organic synthesis include the synthesis of carbamates and ureas from carbonates ([ChCl][ZnCl 2 ] 2 ), [35] amidation reaction (in lipase and metal chloride hydrate‐natural DES), [36] activation of CO 2 and epoxide and their subsequent cycloaddition (in phosphonium‐based DES), [37] synthesis of 3,4 dihydropyrimidin‐2(1 H )‐ones/thiones, [38] synthesis of aminobenzochromenes etc [39] …”