Significance of asymmetric sites in choosing siderophores as deferration agents.

@article{Bergeron2001SignificanceOA,
  title={Significance of asymmetric sites in choosing siderophores as deferration agents.},
  author={Raymond J. Bergeron and Ming Xin and William R. Weimar and Richard E. Smith and Jan Wiegand},
  journal={Journal of medicinal chemistry},
  year={2001},
  volume={44 15},
  pages={2469-78}
}
The syntheses of the microbial iron chelators L-fluviabactin, its unnatural enantiomer, D-fluviabactin, L-homofluviabactin, and L-agrobactin, are described. The key steps involve the selective bis-acylation of the terminal nitrogens of norspermidine, spermidine, or homospermidine with 2,3-bis(benzyloxy)benzoic acid in the presence of 1,1-carbonyldiimidazole, followed by coupling of the N-hydroxysuccinimide ester of CBZ-protected L- or D-threonine with the central nitrogen. The effectiveness of… CONTINUE READING