Synthesis, ligand pK(a), and Fe(III) complexation constants for a series of bipodal dihydroxamic acids.

Journal Article (Journal Article)

The synthesis of four bipodal dihydroxamic acids containing an apical C atom and amide linkages is described, where Ia,b represent "normal" and "retro" hydroxamate isomers: (R)CH[C(=O)NH(CH(2))(2)NHC(=O)(CH(2))(n)()R'](2) (Ia, R = CH(3), R' = N(OH)(C=O)CH(3), n = 2; Ib, R = CH(3), R' = (C=O)N(OH)CH(3), n = 2; Ic, R = CH(3), R' = (C=O)N(OH)CH(3), n = 3; Id, R = C(4)H(9), R' = (C=O)N(OH)CH(3), n = 2.). The pK(a1) and pK(a2) values in aqueous solution are reported, and some degree of cooperativity is noted. Complexation equilibria with Fe(aq)(3+) are described, and values for stepwise and overall equilibrium constants are reported. log beta(230) values for Ia-d are 59.22, 59.45, 58.91, and 58.46, slightly lower than for rhodotorulic acid, although the pFe values for the synthetic siderophores are comparable to that for rhodotorulic acid.

Full Text

Duke Authors

Cited Authors

  • Nguyen-Van-Duong, MK; Guillot, V; Nicolas, L; Gaudemer, A; Lowry, L; Spasojević, I; Crumbliss, AL

Published Date

  • November 5, 2001

Published In

Volume / Issue

  • 40 / 23

Start / End Page

  • 5948 - 5953

PubMed ID

  • 11681910

International Standard Serial Number (ISSN)

  • 0020-1669

Digital Object Identifier (DOI)

  • 10.1021/ic0103143


  • eng

Conference Location

  • United States