Amphiphilic molecules undergo self-assembly in aqueous medium to yield various supramolecular structures depending on their chemical structure and molecular geometry. Among these, lamellar membrane bound vesicles are of special interest due to their resemblance to cellular membranes. We describe the self-assembly of single-chain amide-linked amphiphiles derived from b-D-galactopyranosylamine and various unsaturated fatty acids into vesicles. In contrast, the analogous amphiphiles derived from b-D-glucopyranosylamine self-assemble into nanotubes. Fluorescence spectroscopy, X-ray diffraction, and differential scanning calorimetry are used to determine various physical parameters pertinent to the self-assembly process. The vesicular architecture is characterized using optical microscopy and transmission electron microscopy. We show that the vesicles derived from these amphiphiles can encapsulate molecules of various sizes and host model biochemical reactions such as rolling circle amplification of DNA. Moreover, the single chain glycolipids can self-assemble into variety of lipidic mesophases under various conditions which can be exploited to expand structural and functional diversity in a bottom-up artificial cell. Our work demonstrates that single-chain glycolipid-based amphiphiles could serve as robust building blocks for artificial cells and have potential applications in materials science, drug delivery and microreactor design.

Single-chain synthetic glycolipids: Self-assembly properties and applications to artificial cell development

2019 Fall National Meeting

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