title: Synthesis and biological activity of saccharide based lipophilic siderophore mimetics as potential growth promoters for mycobacteria.
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.
authors: Biomolecular Chemistry, Leibniz Institute for Natural Products Research and Infection Biology - Hans-Knoell-Institute, Beutenbergstrasse 11a, 07745 Jena, Germany.
authors: Peter
authors: P
authors: Gebhardt
authors: Alvin L
authors: AL
authors: Crumbliss
authors: Marvin J
authors: MJ
authors: Miller
authors: Ute
authors: U
authors: Möllmann
mesh_terms: D006877:Hydroxamic Acids / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009161:Mycobacterium / Q000187:drug effects* / Q000254:growth & development; D020102:Mycobacterium smegmatis / Q000187:drug effects / Q000254:growth & development; D017262:Siderophores / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D006877:Hydroxamic Acids; D017262:Siderophores