Composed of one or more fatty acid chains covalently linked to a sugar moiety, glycolipids are amphiphilic in nature and exhibit low toxicity, superior emulsifying activity, and an ability to lower surface tension. These properties make glycolipids the most widely studied biosurfactant and of growing interest in various industries; however, production and isolation of naturally occurring glycolipids can be expensive and produce highly diverse samples. Here we report the synthesis of enantiopure polyamidosaccharides (PASs) with fatty acid initiators to prepare amphiphilic glycolipid mimetics. These polymers adopt a helical secondary structure, self-assemble into nano structures in aqueous solutions, decompose at temperatures between 240-260C, are water soluble, and are non-cytotoxic. Polymers with the C14 hydrophobic chain and shorter hydrophilic chain length exhibited the lowest surface tension (41 mN/m). Overall, these polymers are highly effective glycolipid biosurfactant mimetics, and fill a need for synthetic routes of glycolipid preparation.

Synthesis of polyamidosaccharides with terminal fatty acids as glycolipid biosurfactant mimetics

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