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

• Published in: Journal of agricultural and food chemistry 2020-01, Vol.68 (4), p.989-997
• Main Authors: Nian, Binbin, Cao, Chen, Liu, Yuanfa
• Format: Article
• Language: English
• Subjects: Amino Acids - chemical synthesis; Amino Acids - chemistry; Catalysis; Fungal Proteins - chemistry; Glycerol - chemistry; Hydrogen Bonding; Lipase - chemistry; Solvents - chemistry
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/acs.jafc.9b07446

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.