Synthetic glycolipids are a major target for the production of inexpensive and environmentally friendly surfactants. Rhamnolipid biosurfactants produced by Pseudomonas aeruginosa provided an initial model for the synthesis of a multi-gram scale library of structurally varied glycolipids to test structure/function relationships. With a variety of commercially available mono and disaccharides and their per-acetate derivatives, our work utilizes weak Lewis acids, described as “minimally competent Lewis acids,” to effectively promote the synthesis of a wide variety of alkyl glycosides from lipophilic alcohols and thiols in moderate to high yield. Further interest in the structural modification of synthetic glycolipids has produced both bolaamphiphiles and other chemically-modifiable products. Collaborative efforts allow for the quantification of the surface activity and aggregation properties via Du Noüy ring tensiometry, dynamic light scattering (DLS), steady-state and time-resolved fluorescence quenching, as well as diffusion-ordered spectroscopy (DOSY). Microbiological studies confirm the biodegradability and low toxicity of these novel surfactants and have guided our synthetic efforts. Results from these studies show promise toward the large-scale production and commercial use of these materials. Here we present the synthesis of structurally diverse glycolipids and their evaluation as biosurfactants.

Catalytically promoted glycosylation for the synthesis of O- and S- linked glycolipids

251st National Meeting (2016)

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