Synthesis of Rhamnolipid Derivatives Containing Ester Isosteres.

Rhamnolipids are biosurfactants with many applications, arising from their inherent biological activity and their potential as bioremediation agents. Herein, we report the synthesis of four rhamnolipid derivatives in which the ester linkage connecting the two lipid chains in the natural compound is replaced with amide, ketone, ether, or hydrocarbon functional groups. Such compounds are anticipated to have enhanced hydrolytic stability and thus be useful probes of rhamnolipid-mediated biology and biotechnology.