%0 Journal Article
%T Synthesis of conjugates between oxazolidinone antibiotics and a pyochelin analogue.
%A Paulen A
%A Hoegy F
%A Roche B
%A Schalk IJ
%A Mislin GLA
%J Bioorg Med Chem Lett
%V 27
%N 21
%D 11 2017 1
%M 28947150
%F 2.94
%R 10.1016/j.bmcl.2017.09.039
%X Pseudomonas aeruginosa is a Gram-negative pathogenic bacterium responsible for severe infections, and it is naturally resistant to many clinically approved antibiotic families. Oxazolidinone antibiotics are active against many Gram-positive bacteria, but are inactive against P. aeruginosa. Increasing the uptake of oxazolidinones through the bacterial envelope could lead to an increased antibiotic effect. Pyochelin is a siderophore of P. aeruginosa which delivers external iron to the bacterial cytoplasm and is a potential vector for the development of Trojan Horse oxazolidinone conjugates. Novel pyochelin-oxazolidinone conjugates were synthesized using an unexpectedly regioselective peptide coupling between an amine functionalized pyochelin and oxazolidinones functionalized with a terminal carboxylate.