Synergistic Catalytic Synthesis of Gemini Lipoamino Acids Based on Multiple Hydrogen-Bonding Interactions in Natural Deep Eutectic Solvents-Enzyme System

Abstract

In the previous studies, gemini lipoamino acids (GLAA) were always synthesized by complex multistep organic synthesis, which involved a large number of byproducts and organic solvents. To develop a straightforward, efficient, and renewable synthesis strategy for GLAA, in this study, a type of novel green solvents, natural deep eutectic solvents (NADESs), were adopted as the solvents for these reactions. Five commercial enzymes were involved in the enzyme screening section, and Candida antarctica lipase B (CALB) tended to have the best performance in NADESs systems. The optimization procedure was performed using the Taguchi crossed array method and the highest yield of GLAA (59.14 ± 0.51%) was obtained in choline chloride–glycerol (C–Gly). The purification procedure was carried out with ethyl acetate and water, and the isolate yield ranged from 86.31 ± 2.36 to 91.34 ± 2.26%. With 10 times recycling, the yield of GLAA in C–Gly decreased from 59.14 ± 0.51 to 51.31 ± 0.68%. Interestingly, a synergistic effect of CALB and NADESs was found in the enzymatic synthesis of GLAA, which can be attributed to fatty acids being activated by chloride ions via hydrogen-bonding interactions and resulting in an enhancement in its electron-attracting ability.

Computer-Aided Lipase Engineering for Improving Their Stability and Activity in the Food Industry: State of the Art

“…Coincidentally, D-xylose laurate esters and L-arabinose laurate esters can be obtained via the esterification of sugars and vinyl laurate in 2-methyl-2-butanol with the catalysis of Novozyme 435 [52]. The lipase-catalyzed acylation reaction has also been widely investigated recently, and it has been found that CALB has a higher efficiency than D-Aminoacylase from Escherichia coli, and lipase from porcine pancreas, et al in the acylation of fatty acids and amino acids [1,53,54].…”

“…With the deepening of investigations, researchers have also found that the catalytic efficiency of lipases, especially in the esterification reaction and acylation reaction, is significantly affected by the solvent [1,[55][56][57]. Most recently, some novel green solvents were found to have great advantages in terms of the dissolution substrate and low-cost preparation, and are easy to separate and purify in enzymatic reactions.…”

“…With the depletion of nonrenewable resources and the increase in environmental pollution, organic reactions, which consume a lot of organic solvent s, are considered to be environmentally unfriendly [1,2]. Moreover, traditional chemical esterification often uses toxic and corrosive catalysts, such as sulfuric acid/sodium hydroxide, as well as using elevated reaction temperatures, which can also result in generating random nonselective reactions.…”

Asymmetric Bioreduction of Ethyl 4-Chloroacetoacetate into Ethyl 4-Chloro-3-hydroxybutyrate by Recombinant Escherichia coli CgCR in Ethyl Acetate-Betaine:Lactic Acid-Water

“…Deep eutectic solvents (DESs), which can be prepared by blending a hydrogen-bond-acceptor (e.g., choline chloride) and a hydrogen-bond-donor (e.g., amines, carboxylic acids, and polyols) [41][42][43], are recognized as green solvents. They have been extensively utilized as a chemical or biochemical reaction medium for enhancing catalytic efficiency [44][45][46][47]. Some DESs have been applied as a tool for biocatalysis, either as solvents or as separative agents to overcome challenging workup procedures [48][49][50].…”