Journal of the American Chemical Society, Vol.118, No.49, 12368-12375, 1996
Fluorescently-Labeled Ferrichrome Analogs as Probes for Receptor-Mediated, Microbial Iron Uptake
Biomimetic analogs 1 of the microbial siderophore (iron carrier) ferrichrome were labeled with a fluorescent marker at a site which does not interfere with iron binding or receptor recognition to provide iron(III) carriers 5 and 10 (Figure 1). These carriers were built from a tetrahedral carbon as an anchor which was symmetrically extended by three converging iron-binding chains and a single, exogenous anthracenyl residue. Carriers 5 varied in the nature of the amino acids (G = glycyl, A = alanyl and L = leucyl) Linking the anchor with the iron-binding hydroxamate groups, while the alanyl derivative 10A differed from 5A in the spacer between the anthracenyl label and the anchor.
Keywords:CHIRAL SIDEROPHORE ANALOGS;BIOMIMETIC ANALOGS;MOLECULAR RECOGNITION;PSEUDOMONAS-PUTIDA;FERRIOXAMINE-B;IRON(III);CHEMISTRY;FUNGI;ENTEROBACTIN;TRANSPORT