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JBIC Journal of Biological Inorganic Chemistry

, Volume 23, Issue 7, pp 969–982 | Cite as

The chemical biology and coordination chemistry of putrebactin, avaroferrin, bisucaberin, and alcaligin

  • Rachel CoddEmail author
  • Cho Zin Soe
  • Amalie A. H. Pakchung
  • Athavan Sresutharsan
  • Christopher J. M. Brown
  • William Tieu
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Part of the following topical collections:
  1. Alison Butler: Papers in Celebration of Her 2018 ACS Alfred Bader Award in Bioorganic or Bioinorganic Chemistry

Abstract

Dihydroxamic acid macrocyclic siderophores comprise four members: putrebactin (putH2), avaroferrin (avaH2), bisucaberin (bisH2), and alcaligin (alcH2). This mini-review collates studies of the chemical biology and coordination chemistry of these macrocycles, with an emphasis on putH2. These Fe(III)-binding macrocycles are produced by selected bacteria to acquire insoluble Fe(III) from the local environment. The macrocycles are optimally pre-configured for Fe(III) binding, as established from the X-ray crystal structure of dinuclear [Fe2(alc)3] at neutral pH. The dimeric macrocycles are biosynthetic products of two endo-hydroxamic acid ligands flanked by one amine group and one carboxylic acid group, which are assembled from 1,4-diaminobutane and/or 1,5-diaminopentane as initial substrates. The biosynthesis of alcH2 includes an additional diamine C-hydroxylation step. Knowledge of putH2 biosynthesis supported the use of precursor-directed biosynthesis to generate unsaturated putH2 analogues by culturing Shewanella putrefaciens in medium supplemented with unsaturated diamine substrates. The X-ray crystal structures of putH2, avaH2 and alcH2 show differences in the relative orientations of the amide and hydroxamic acid functional groups that could prescribe differences in solvation and other biological properties. Functional differences have been borne out in biological studies. Although evolved for Fe(III) acquisition, solution coordination complexes have been characterised between putH2 and oxido-V(IV/V), Mo(VI), or Cr(V). Retrosynthetic analysis of 1:1 complexes of [Fe(put)]+, [Fe(ava)]+, and [Fe(bis)]+ that dominate at pH < 5 led to a forward metal-templated synthesis approach to generate the Fe(III)-loaded macrocycles, with apo-macrocycles furnished upon incubation with EDTA. This mini-review aims to capture the rich chemistry and chemical biology of these seemingly simple compounds.

Graphical abstract

Keywords

Siderophores Hydroxamic acid macrocycles Putrebactin Precursor-directed biosynthesis Metal-templated synthesis 

Notes

Acknowledgements

Alison Butler and Kathleen M. Ledyard are acknowledged for the discovery of putrebactin, which has fuelled a significant amount of research activity in our group and others. Alison Butler is also acknowledged for her generosity in sharing her expertise and passion for siderophore chemistry and her effective style of mentoring and support of scientists in the US and beyond. Alison Butler and Thomas Böttcher are kindly acknowledged for providing the X-ray structure coordinates for putH2 and avaH2, respectively. This work was supported by the Australian Research Council (ARC DP140100092) and the Australian Commonwealth Government (Australian Postgraduate Awards to A.S. and C.J.M.B.). The University of Sydney is acknowledged for funding (co-funded Postgraduate Scholarship to C.Z.S. and to A.A.H.P.).

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Copyright information

© SBIC 2018

Authors and Affiliations

  • Rachel Codd
    • 1
    Email author
  • Cho Zin Soe
    • 1
  • Amalie A. H. Pakchung
    • 1
  • Athavan Sresutharsan
    • 1
  • Christopher J. M. Brown
    • 1
  • William Tieu
    • 1
  1. 1.School of Medical Sciences (Pharmacology) and Bosch InstituteThe University of SydneySydneyAustralia

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