Synthesis of a glycolipid library based on immunostimulatory and bioremediation rhamnolipids produced by Pseudomonas aeruginosa.

摘要

Rhamnolipids are exogenous glycolipids produced by Pseudomonas aeruginosa and have been shown to stimulate the mammalian innate immune system via a toll-like receptor-independent mechanism. Additionally, rhamnolipids exhibit anti-microbial properties and there have been few studies to elucidate their mechanism of action. Rhamnolipids have also been shown to have surface active properties comparable to synthetic surfactants, and their use is advantageous as they are ecologically tolerated. These surface active properties have been exploited for the remediation of soils contaminated with oils, heavy metals and organic pesticides.;Here, two small glycolipid libraries have been synthesized to probe structure activity relationships for activation of the innate immune system and, the remediation properties of the rhamnolipid scaffold. Key transformations in these syntheses involve rhodium-catalyzed asymmetric β-keto ester reduction and trichloroacetimidate mediated glycosylation. Also, a new glycosylation procedure involving carbontetraiodide and triphenylphosphine has been explored.