BioMetals

, Volume 21, Issue 1, pp 41–51

Synthesis and biological activity of saccharide based lipophilic siderophore mimetics as potential growth promoters for mycobacteria

  • Peter Gebhardt
  • Alvin L. Crumbliss
  • Marvin J. Miller
  • Ute Möllmann
Article

DOI: 10.1007/s10534-007-9091-x

Cite this article as:
Gebhardt, P., Crumbliss, A.L., Miller, M.J. et al. Biometals (2008) 21: 41. doi:10.1007/s10534-007-9091-x

Abstract

Siderophores based on sugar backbones substituted at the 2,3,4- or 2,3,6 positions with hydroxamic or retro-hydroxamic acid chelating units were synthesized and characterized. The alkyl terminus of the iron-coordinating side chain units facilitate lipophilic interactions. Iron coordination properties and complex stability were investigated by ESI-MS and the CAS-Test. The results were correlated to structure activity relationships determined by microbial growth promotion studies under iron limited conditions using wild type strains and iron transport mutants of Mycobacterium smegmatis.

Keywords

Siderophore synthesisHydroxamateSugar backboneMycobacteria

Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • Peter Gebhardt
    • 1
  • Alvin L. Crumbliss
    • 2
  • Marvin J. Miller
    • 3
  • Ute Möllmann
    • 4
  1. 1.Biomolecular ChemistryLeibniz Institute for Natural Products Research and Infection Biology – Hans-Knoell-InstituteJenaGermany
  2. 2.Department of ChemistryDuke UniversityDurhamUSA
  3. 3.Department of Chemistry and BiochemistryUniversity of Notre DameNotre DameUSA
  4. 4.Applied MicrobiologyLeibniz Institute for Natural Products Research and Infection Biology – Hans-Knoell-InstituteJenaGermany