{"title":"Optimization of Enzymatic Synthesis of D-Glucose-Based Surfactants Using Supported Aspergillus niger Lipase as Biocatalyst","authors":"Alexis Spalletta, N. Joly, Patrick Martin","doi":"10.3390/chemistry5030127","DOIUrl":null,"url":null,"abstract":"Surfactants are amphiphilic molecules with the ability to modify the surface tension between two surfaces. They can be obtained by various methods, the main one being synthetic, from petroleum-based substrates. Their universal use in a wide range of fields has created a global market and, consequently, ecological, and economic expectations for their production. Biocatalyzed processes, involving enzymes, can address this objective with processes complying with the principles of green chemistry: energy saving, product selectivity, monodispersity, and reduction in the use of solvents, with energy eco-efficiency. For example, fatty-acid carbohydrate esters are biobased surfactants that can be synthesized by lipases. In this work, we were interested in the synthesis of D-glucose lauric ester, which presents interesting properties described in the literature, with Aspergillus niger lipase, rarely described with sugar substrates. We optimized the synthesis for different parameters and reaction media. This lipase appeared to be highly selective for 6-O-lauroyl-D-glucopyranose. However, the addition of DMSO (dimethyl sulfoxide) as a co-solvent displays a duality, increasing yields but leading to a loss of selectivity. In addition, DMSO generates more complex and energy-intensive purification and processing steps. Consequently, a bio-sourced alternative as co-solvent with 2MeTHF3one (2-methyltetrahydrofuran-3-one) is proposed to replace DMSO widely described in the literature.","PeriodicalId":29793,"journal":{"name":"Precision Chemistry","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2023-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Precision Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.3390/chemistry5030127","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
Surfactants are amphiphilic molecules with the ability to modify the surface tension between two surfaces. They can be obtained by various methods, the main one being synthetic, from petroleum-based substrates. Their universal use in a wide range of fields has created a global market and, consequently, ecological, and economic expectations for their production. Biocatalyzed processes, involving enzymes, can address this objective with processes complying with the principles of green chemistry: energy saving, product selectivity, monodispersity, and reduction in the use of solvents, with energy eco-efficiency. For example, fatty-acid carbohydrate esters are biobased surfactants that can be synthesized by lipases. In this work, we were interested in the synthesis of D-glucose lauric ester, which presents interesting properties described in the literature, with Aspergillus niger lipase, rarely described with sugar substrates. We optimized the synthesis for different parameters and reaction media. This lipase appeared to be highly selective for 6-O-lauroyl-D-glucopyranose. However, the addition of DMSO (dimethyl sulfoxide) as a co-solvent displays a duality, increasing yields but leading to a loss of selectivity. In addition, DMSO generates more complex and energy-intensive purification and processing steps. Consequently, a bio-sourced alternative as co-solvent with 2MeTHF3one (2-methyltetrahydrofuran-3-one) is proposed to replace DMSO widely described in the literature.
表面活性剂是两亲性分子,具有改变两个表面之间表面张力的能力。它们可以通过各种方法获得,主要方法是从石油基基质中合成的。它们在广泛领域的普遍使用创造了一个全球市场,因此也产生了对其生产的生态和经济期望。涉及酶的生物催化过程可以通过符合绿色化学原则的过程来实现这一目标:节能、产品选择性、单分散性和减少溶剂的使用,并具有能源生态效率。例如,脂肪酸碳水化合物酯是可以由脂肪酶合成的生物基表面活性剂。在这项工作中,我们对d -葡萄糖月桂酸酯的合成很感兴趣,它在文献中描述了一些有趣的性质,黑曲霉脂肪酶很少用糖底物描述。在不同的工艺参数和反应介质条件下对合成工艺进行了优化。该脂肪酶对6- o -月桂醇- d -葡萄糖醛酸具有高度选择性。然而,加入DMSO(二甲基亚砜)作为共溶剂显示出二元性,增加了产率,但导致选择性的损失。此外,DMSO产生更复杂和能源密集型的净化和处理步骤。因此,提出了一种生物源替代品,以2MeTHF3one(2-甲基四氢呋喃-3-one)作为共溶剂来取代文献中广泛描述的DMSO。
期刊介绍:
Chemical research focused on precision enables more controllable predictable and accurate outcomes which in turn drive innovation in measurement science sustainable materials information materials personalized medicines energy environmental science and countless other fields requiring chemical insights.Precision Chemistry provides a unique and highly focused publishing venue for fundamental applied and interdisciplinary research aiming to achieve precision calculation design synthesis manipulation measurement and manufacturing. It is committed to bringing together researchers from across the chemical sciences and the related scientific areas to showcase original research and critical reviews of exceptional quality significance and interest to the broad chemistry and scientific community.