Departamento de Química, Universidad Nacional de Rio Cuarto, Agencia Postal 3, C.P. X5804BYA, Ruta Nacional 36, km 601, Rio Cuarto, Córdoba, Argentina and Instituto de Desarrollo Agroindustrial y de la Salud (IDAS), Universidad Nacional de Río Cuarto, Agencia Postal 3, C.P. X5804BYA, Ruta Nacional 36, km 601, Río Cuarto, Córdoba, Argentina.
Departamento de Química, Universidad Nacional de Rio Cuarto, Agencia Postal 3, C.P. X5804BYA, Ruta Nacional 36, km 601, Rio Cuarto, Córdoba, Argentina.
Org Biomol Chem. 2021 Jun 9;19(22):4969-4977. doi: 10.1039/d0ob02371j.
In the last decade, the nature of the nonpolar solvents that can be part of reverse micelles (RMs) has been the topic of several investigations to improve their applications. In this sense, the hydrolysis of 1-naphthyl phosphate catalyzed by the enzyme alkaline phosphatase (AP) was used as a probe to investigate the effect of the change of the external solvent on RMs formulated with the anionic surfactant sodium diethylhexyl sulfosuccinate (AOT). As external nonpolar solvents, two biocompatible lipophilic esters, isopropyl myristate and methyl laurate, and the traditional nonpolar solvents, n-heptane and benzene, were used. The results were compared among the RMs investigated and with the reaction in homogeneous media. Thus, the effect of the nanoconfinement as well as the impact of the replacement of a conventional external nonpolar solvent by biocompatible solvents were analyzed. The results indicate that the catalytic efficiency in the AOT RMs is larger than that in homogeneous media, denoting a different hydration level over the AP enzyme, which is directly related to the different degrees of nonpolar solvent penetration to the RM interface. Our findings demonstrated that toxic solvents such as n-heptane and benzene can be replaced by nontoxic ones (isopropyl myristate or methyl laurate) in AOT RMs without affecting the performance of micellar systems as nanoreactors, making them a green and promising alternative toward efficient and sustainable chemistry.
在过去的十年中,能够成为反胶束(RM)一部分的非极性溶剂的性质一直是几项研究的主题,目的是改进它们的应用。在这种情况下,酶碱性磷酸酶(AP)催化的 1-萘基磷酸酯的水解被用作探针,以研究改变外部溶剂对用阴离子表面活性剂二乙基己基琥珀酸酯(AOT)配制的 RM 的影响。作为外部非极性溶剂,使用了两种生物相容性亲脂性酯,即肉豆蔻酸异丙酯和月桂酸甲酯,以及传统的非极性溶剂正庚烷和苯。将结果与均相介质中的反应进行了比较。因此,分析了纳米约束的影响以及用生物相容性溶剂替代传统外部非极性溶剂的影响。结果表明,在 AOT RM 中的催化效率大于均相介质中的催化效率,这表示 AP 酶的水合程度不同,这与非极性溶剂渗透到 RM 界面的不同程度直接相关。我们的研究结果表明,在不影响胶束体系作为纳米反应器的性能的情况下,AOT RM 中的有毒溶剂(如正庚烷和苯)可以被无毒溶剂(肉豆蔻酸异丙酯或月桂酸甲酯)替代,这为高效和可持续的化学提供了一种绿色且有前景的替代方法。