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Synergistic Catalytic Synthesis of Gemini Lipoamino Acids Based on Multiple Hydrogen-Bonding Interactions in Natural Deep Eutectic Solvents-Enzyme System.
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2020-01-14 , DOI: 10.1021/acs.jafc.9b07446
Binbin Nian 1 , Chen Cao 1 , Yuanfa Liu 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2020-01-14 , DOI: 10.1021/acs.jafc.9b07446
Binbin Nian 1 , Chen Cao 1 , Yuanfa Liu 1
Affiliation
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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.
中文翻译：
基于天然深共晶溶剂-酶系统中多个氢键相互作用的协同催化合成双子叶脂氨基酸。
在以前的研究中，双子座脂氨基酸（GLAA）总是通过复杂的多步有机合成来合成，其中涉及大量的副产物和有机溶剂。为了开发用于GLAA的简单，有效和可再生的合成策略，在本研究中，一种新型绿色溶剂，即天然深共熔溶剂（NADES）被用作这些反应的溶剂。酶筛选部分涉及五种商业酶，南极假丝酵母脂肪酶B（CALB）在NADESs系统中往往表现最佳。使用Taguchi交叉阵列方法进行了优化程序，在氯化胆碱-甘油（C-Gly）中获得了最高的GLAA收率（59.14±0.51％）。纯化步骤用乙酸乙酯和水进行，分离物的产率为86。31±2.36至91.34±2.26％。经过10次循环，C-Gly中GLAA的产率从59.14±0.51降低至51.31±0.68％。有趣的是，在GLAA的酶促合成中发现了CALB和NADES的协同作用，这可以归因于脂肪酸通过氢键相互作用被氯离子激活，从而增强了其电子吸引能力。
更新日期：2020-01-14
中文翻译：
基于天然深共晶溶剂-酶系统中多个氢键相互作用的协同催化合成双子叶脂氨基酸。
在以前的研究中，双子座脂氨基酸（GLAA）总是通过复杂的多步有机合成来合成，其中涉及大量的副产物和有机溶剂。为了开发用于GLAA的简单，有效和可再生的合成策略，在本研究中，一种新型绿色溶剂，即天然深共熔溶剂（NADES）被用作这些反应的溶剂。酶筛选部分涉及五种商业酶，南极假丝酵母脂肪酶B（CALB）在NADESs系统中往往表现最佳。使用Taguchi交叉阵列方法进行了优化程序，在氯化胆碱-甘油（C-Gly）中获得了最高的GLAA收率（59.14±0.51％）。纯化步骤用乙酸乙酯和水进行，分离物的产率为86。31±2.36至91.34±2.26％。经过10次循环，C-Gly中GLAA的产率从59.14±0.51降低至51.31±0.68％。有趣的是，在GLAA的酶促合成中发现了CALB和NADES的协同作用，这可以归因于脂肪酸通过氢键相互作用被氯离子激活，从而增强了其电子吸引能力。
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