Synthesis and siderophore activity of vibrioferrin and one of its diastereomeric isomers

Abstract

Total synthesis of vibrioferrin (1), a siderophore, was achieved via a chiral dibenzyl citrate obtained by optical resolution. The citrate moiety of vibrioferrin was determined to have the R configuration and one of the diastereomeric isomers (1b) of 1 did not exhibit siderophore activity.