title: Trishydroxamates and triscatecholates based on monosaccharides and myo-inositol as artificial siderophores.
abstract: New trishydroxamates and triscatecholates based on methyl alpha-D-glucopyranoside, methyl alpha-D-galactopyranoside, methyl alpha-D-ribopyranoside and methyl alpha-D-xylopyranoside as well as on 1,3,5-tri-O-benzyl-myo-inositol were synthesized. N-Methylsuccinohydroxamate, N-methylglutarohydroxamate and their O-benzoyl derivatives were used as hydroxamate moieties. 2,3-Dihydroxybenzoyl derivatives and acylated compounds as well as 2,3- and 3,4-dihydroxybenzylidenehydrazino derivatives, partly with spacer groups, were utilized as catecholate components. The siderophore activity of the prepared siderophore analogues was examined by a growth promotion assay with various Gram-negative bacteria and mycobacteria and by the CAS-assay. Some trishydroxamates and triscatecholates showed siderophore activity on Gram-negative bacteria and triscatecholates on mycobacteria. Iron complexes of the trishydroxamates act as siderophores for all types of iron transport mutants. The recognition and uptake specificity of these compounds was studied by E. coli siderophore receptor and iron transport mutants. Structure activity correlations are discussed.
authors.affiliation: Hans Knöll-Institut für Naturstoff-Forschung, Jena, Germany.
authors.forename: Susanne
authors.initials: S
authors.lastname: Heggemann
authors.forename: Ute
authors.initials: U
authors.lastname: Möllmann
authors.forename: Peter
authors.initials: P
authors.lastname: Gebhardt
authors.forename: Lothar
authors.initials: L
authors.lastname: Heinisch
mesh_terms: D002396:Catechols / Q000138:chemical synthesis* / Q000737:chemistry*; D006877:Hydroxamic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D007294:Inositol / Q000737:chemistry*; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry*; D017262:Siderophores / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D002396:Catechols; D006877:Hydroxamic Acids; D009005:Monosaccharides; D017262:Siderophores; D007294:Inositol