水相无催化剂合成赖氨酸基两性两亲分子用于多功能应用：表征及 pH 响应乳化性能。
Water-mediated catalyst-free synthesis of lysine-based ampholytic amphiphiles for multipurpose applications: Characterization and pH-responsive emulsifying properties.
机构信息
School of Food Science and Engineering, South China University of Technology, No. 381, Wushan Road, Tianhe District, Guangzhou 510640, China; Department of Engineering, Faculty of Science and Technology, Aarhus University, Gustav Wieds vej 10, 8000 Aarhus C, Denmark.
Department of Engineering, Faculty of Science and Technology, Aarhus University, Gustav Wieds vej 10, 8000 Aarhus C, Denmark.
出版信息
J Colloid Interface Sci. 2019 Oct 15;554:404-416. doi: 10.1016/j.jcis.2019.06.104. Epub 2019 Jul 2.
A novel series of lysine-based ampholytic amphiphiles, with alkylsuccinic anhydrides of varying chain lengths as hydrophobic acylating agents, were synthesized in medium to high yield (50.23-90.15%) based on a facile, catalyst-free method in water medium; and structurally confirmed by mass spectrometry (MS), Fourier transform infra-red (FTIR) spectroscopy, and H/C nuclear magnetic resonances (NMR) analysis. The resulting compounds were subjected to pH-dependent amphiphilic property, ferrous ion chelating, DPPH antioxidant capacity, and cytotoxicity analyses. Results showed that CMC values decrease, γ value increase, and emulsion stability increase with the increase of medium pH, suggesting that the surface activity of synthetic compounds at air/water and oil/water interface under neutral and alkaline conditions was remarkably higher than that under acidic condition. Lauryl O-acylated malic lysine (compound 4b) presented excellent foaming ability close to commercial detergent sodium dodecyl sulphate; dodecyl succinic lysine (compound 4a) afforded highly stable o/w nanoemulsion. Moreover, compound 4b displayed comparable ferrous ion chelating property to lysine and 2,2-diphenyl-1-picrylhydrazyl (DPPH) antioxidative capacity similar to a commercial food ingredient, diacetyl tartaric acid esters of mono- and di-glycerides (DATEM), indicating its multi-faceted functionalities. A cytotoxicity study of compounds 3b &4b showed that they were non-toxic. Thus, these novel ampholytic amphiphiles may find multi-purpose applications in food, detergent, pharmaceutical, and cosmetic industry.
一种新型赖氨酸两性离子两亲分子，以不同链长的烷基琥珀酸酐为疏水性酰化剂，在水介质中采用简单、无催化剂的方法以中等到高产率（50.23-90.15%）合成；通过质谱（MS）、傅里叶变换红外（FTIR）光谱和 H/C 核磁共振（NMR）分析得到结构确证。所得化合物进行了 pH 依赖性两亲性、亚铁离子螯合、DPPH 抗氧化能力和细胞毒性分析。结果表明，CMC 值降低，γ 值增加，乳液稳定性随着介质 pH 的增加而增加，这表明在中性和碱性条件下，合成化合物在气/水和油/水界面的表面活性明显高于酸性条件下的表面活性。月桂酰化马来酸赖氨酸（化合物 4b）具有接近商业洗涤剂十二烷基硫酸钠的优异发泡能力；十二烷基琥珀酸赖氨酸（化合物 4a）形成高度稳定的 o/w 纳米乳液。此外，化合物 4b 显示出与赖氨酸相当的亚铁离子螯合性能和与商业食品成分二乙酰基酒石酸单甘油酯和二甘油酯（DATEM）相当的 DPPH 抗氧化能力，表明其具有多方面的功能。化合物 3b 和 4b 的细胞毒性研究表明它们无毒。因此，这些新型两性离子两亲分子可能在食品、洗涤剂、制药和化妆品行业有多种用途。
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