Alkyl-mannoside derivatives: Glycolipids able to form big size aggregates

Abstract

Three different series of alkyl mannoside derivatives have been synthesized, designing the hydrophobic portion to provide different topology to the surfactant and, hence, modulating their aggregation properties. The aggregates formed were characterized using both physical and photophysical methodologies, such as surface tension, dynamic light scattering, and emission of selected fluorescent probes. The non‐ionic sugar surfactants have been widely used in studies of membrane solubilization and protein purification. Indeed, mannoside unit, nonionic and hydrophilic, can be selectively recognized by several lectins, which are proteins present in different membranes. Then, the specific interactions of these derivatives incorporated into synthetic bilayers with lectins have been studied and reported. In this work, monoalkyl derivatives with a presumably conical shape and dialkyl derivatives with cylindrical ones, including also a third family with a hydrophilic spacer were studied. These compounds are able to self‐ aggregate to form micelle like structures or bilayers despite their topology. Additionally, they are able to form bilayers, using cosurfactants like cholesterol.