State Key Laboratory of Materials-Oriented Chemical Engineering, School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing 210009, Jiangsu Province, People's Republic of China.
College of Food Science, Northeast Agricultural University, Harbin 150030, China.
J Agric Food Chem. 2024 Oct 23;72(42):23401-23410. doi: 10.1021/acs.jafc.4c06877. Epub 2024 Oct 10.
Glucose esters, heralded for their emulsifying and solubilizing properties, have found increasing application in food, pharmaceutical, and cosmetic sectors. However, the environmental impact of chemical synthesis and the problem of enzyme inactivation in enzymatic synthesis have hindered their application. To this end, deep eutectic solvents (DESs) with stabilized enzyme activity and better solubility properties are considered a promising solution. In the study, 12 kinds of hydrophilic DESs and 22 kinds of hydrophobic DESs were screened, and we examined their efficiency in the synthesis of glucose esters. The results indicated that d,l-menthol-based DESs have excellent performance, with the highest yield of 92.85%. The molecular dynamics simulations suggested that it can be attributed to DESs changing the size of substrate binding pocket, which in turn affects the substrate anchoring ability and the catalytic efficiency of lipase. To further evaluate the effects of the solvent on the substrate anchoring ability of enzymes, a novel strategy, namely, substrate anchoring index, which is based on the stability of the tetrahedral intermediate, was proposed and used for the designing of more efficient DESs. Fortunately, novel DESs based on cyclohexanone (menthol analogues) were successfully developed with a yield of 98.85%.
葡萄糖酯因其乳化和增溶性能而备受关注，已在食品、制药和化妆品等领域得到了越来越广泛的应用。然而，化学合成的环境影响和酶合成中酶失活的问题限制了它们的应用。为此，具有稳定酶活性和更好溶解性能的深共熔溶剂（DESs）被认为是一种很有前途的解决方案。在这项研究中，筛选了 12 种亲水性 DESs 和 22 种疏水性 DESs，并考察了它们在葡萄糖酯合成中的效率。结果表明，基于 d,l-薄荷醇的 DESs 具有优异的性能，产率最高可达 92.85%。分子动力学模拟表明，这可以归因于 DESs 改变了底物结合口袋的大小，从而影响了底物的锚固能力和脂肪酶的催化效率。为了进一步评估溶剂对酶的底物锚固能力的影响，提出了一种新的策略，即基于四面体中间体稳定性的底物锚固指数，用于设计更有效的 DESs。幸运的是，成功开发了基于环己酮（薄荷醇类似物）的新型 DESs，产率高达 98.85%。
