Synthesis and activity of p-azidobenzoyloxyferricrocin, a photoactivatable analog of ferrichrome.
p-azidobenzoyloxy desferriferricrocin (AF) 2, a photoactivatable analog of ferrichrome, was prepared by selective acylation of the serine group of ferricrocin 1 in two steps: transesterification of ferricrocin followed by demetallation. A model compound, (L) 2-benzyloxycarbonylamino-3-p-azidobenzoyloxy N-isopropyl propionamide 8, was separately synthesized in order to set up optimal transesterification conditions to avoid alpha, beta-elimination or epimerization of serine. Binding of iron-loaded AF (FeAF) to the FhuA outer membrane receptor protein of Escherichia coli AB2847 was demonstrated by inhibition of ferrichrome transport, interference with the infection by the bacteriophage phi 80 and with killing of cells by albomycin and colicin M. FeAF transported iron only weakly which indicates that the photoaffinity moiety is incompatible with transport or intracellular iron release from the siderophore.
Laboratoire de Chimie Microbienne, Associé au C.N.R.S., Ecole Supérieure de Biotechnologie de Strasbourg, Illkirch, France.
A L
AL
Salah el Din
V
V
Braun
M A
MA
Abdallah
D000345:Affinity Labels / Q000138:chemical synthesis* / Q000378:metabolism; D001386:Azides / Q000138:chemical synthesis* / Q000378:metabolism; D005291:Ferrichrome / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000378:metabolism; D010782:Photolysis
D000345:Affinity Labels; D001386:Azides; C120270:p-azidobenzoyloxyferricrocin; D005291:Ferrichrome