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.