Synthesis and biological activity of saccharide based lipophilic siderophore mimetics as potential growth promoters for mycobacteria |
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| Authors: | Peter Gebhardt Alvin L. Crumbliss Marvin J. Miller Ute Möllmann |
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| Affiliation: | (1) Biomolecular Chemistry, Leibniz Institute for Natural Products Research and Infection Biology – Hans-Knoell-Institute, Beutenbergstrasse 11a, 07745 Jena, Germany;(2) Department of Chemistry, Duke University, Durham, NC 27708-0346, USA;(3) Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN 46556, USA;(4) Applied Microbiology, Leibniz Institute for Natural Products Research and Infection Biology – Hans-Knoell-Institute, Beutenbergstrasse 11a, 07745 Jena, Germany |
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| 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. |
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| Keywords: | Siderophore synthesis Hydroxamate Sugar backbone Mycobacteria |
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