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Unsaturated macrocyclic dihydroxamic acid siderophores produced by Shewanella putrefaciens using precursor-directed
1School of Medical Sciences (Pharmacology) and Bosch Institute, The University of Sydney , Sydney, New South Wales 2006, Australia.
ACS Chemical Biology
|February 4, 2014
Summary
Researchers synthesized novel unsaturated siderophores, E,E-putrebactene and E-putrebactene, by modifying iron acquisition pathways in Shewanella putrefaciens. These findings reveal insights into siderophore function and offer new avenues for molecular diversity.
Area of Science:
- Microbiology and Biochemistry
- Chemical Biology
- Biotechnology
Background:
- Shewanella putrefaciens utilizes putrebactin (pbH2), a macrocyclic dihydroxamic acid, for iron acquisition.
- Putrebactin biosynthesis depends on endogenous 1,4-diaminobutane (DB), derived from l-ornithine via ornithine decarboxylase (ODC).
Purpose of the Study:
- To investigate the biosynthesis of novel siderophore analogs by manipulating endogenous DB levels in S. putrefaciens.
- To characterize the properties of newly synthesized unsaturated siderophores and their iron-binding capabilities.
Main Methods:
- Attenuated endogenous DB levels using an ODC inhibitor (DBO).
- Introduced alternative diamine substrates: (15)N2-1,4-diaminobutane ((15)N2-DB) and 1,4-diamino-2(E)-butene (E-DBE).
- Analyzed synthesized siderophores and their Fe(III) complexes using Liquid Chromatography-Mass Spectrometry (LC-MS).
Main Results:
- Successfully synthesized (15)N-labeled pbH2 ((15)N4-pbH2) and unsaturated variants: E,E-putrebactene (E,E-pbeH2) and E-putrebactene (E-pbxH2).
- Demonstrated 1:1 complex formation between Fe(III) and all synthesized siderophores (pbH2, (15)N4-pbH2, E,E-pbeH2, E-pbxH2).
- Established an order of Fe(III) solubility gain: pbH2 > E-pbxH2 > E,E-pbeH2, suggesting a reason for nature's preference for saturated siderophores.
Conclusions:
- Identified the first unsaturated macrocyclic dihydroxamic acid siderophores, expanding the known structural diversity of these iron-chelating compounds.
- The study provides mechanistic insights into siderophore biosynthesis and function, highlighting the role of saturation in Fe(III) solubilization.
- Unsaturated siderophores offer a platform for ex situ chemical modifications, opening new avenues for creating diverse siderophore analogs.
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