Please use this identifier to cite or link to this item:
https://hdl.handle.net/2440/123303
Citations | ||
Scopus | Web of Science® | Altmetric |
---|---|---|
?
|
?
|
Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Sresutharsan, A. | - |
dc.contributor.author | Tieu, W. | - |
dc.contributor.author | Richardson-Sanchez, T. | - |
dc.contributor.author | Soe, C.Z. | - |
dc.contributor.author | Codd, R. | - |
dc.date.issued | 2017 | - |
dc.identifier.citation | Journal of Inorganic Biochemistry, 2017; 177:344-351 | - |
dc.identifier.issn | 0162-0134 | - |
dc.identifier.issn | 1873-3344 | - |
dc.identifier.uri | http://hdl.handle.net/2440/123303 | - |
dc.description | Available online 01 August 2017 | - |
dc.description.abstract | Macrocyclic hydroxamic acids coordinate Fe(III) with high affinity as part of siderophore-mediated bacterial iron acquisition. Trimeric hydroxamic acid macrocycles, such as desferrioxamine E (DFOE), are prevalent in nature, with fewer dimeric macrocycles identified, including putrebactin (pbH2), avaroferrin (avH2), bisucaberin (bsH2) and alcaligin (alH2). This work used metal-templated synthesis (MTS) to pre-assemble complexes between one equivalent of Fe(III) and two equivalents of 4-((4-aminobutyl)(hydroxy)amino)-4-oxobutanoic acid (BBH) or 4-((5-aminopentyl)(hydroxy)amino)-4-oxobutanoic acid (PBH). Following peptide coupling, the respective Fe(III) complexes of pbH2 or bsH2 were formed, which analysed by LC-MS under acidic pH as [Fe(pb)]+ ([M]+, m/zobs 426.1) or [Fe(bs)]+ ([M]+, m/zobs 454.2). The mixed-ligand 1:1:1 Fe(III):BBH:PBH system furnished [Fe(pb)]+ and [Fe(bs)]+, together with chimeric [Fe(av)]+ ([M]+, m/zobs 440.2). The deviation from the expected 1:2:1 distribution of [Fe(pb)]+:[Fe(av)]+:[Fe(bs)]+ to 1:3.2:1.6 suggested the MTS-mediated formation of dimeric macrocycles could be influenced by steric effects in the pre-complex and/or cavity size, as governed by the monomer. 21-Membered avH2 defined the lower boundary of the optimal architecture. Mixed-ligand MTS between Fe(III):PBH-d4:ret-PBH at 1:1.5:1.5, where ret-PBH=3-(6-amino-N-hydroxyhexanamido)propanoic acid, gave four Fe(III)-loaded trimeric hydroxamic acid macrocycles in a distribution of 1.0:3.0:2.9:1.1 that closely matched the expected distribution 1:3:3:1 for a system without any kinetic and/or thermodynamic bias. Apo-macrocycles pbH2, avH2 and bsH2 were produced upon incubation with diethylenetriaminepentaacetic acid (DTPA) and co-eluted with a biosynthetic mixture of the native macrocycles. The work has demonstrated the utility of single- and mixed-ligand MTS for producing a variety of homo- and heteroleptic dimeric hydroxamic acid macrocycles as Fe(III) complexes and free ligands. | - |
dc.description.statementofresponsibility | Athavan Sresutharsan, William Tieu, Tomas Richardson-Sanchez, Cho Zin Soe, Rachel Codd | - |
dc.language.iso | en | - |
dc.publisher | Elsevier | - |
dc.rights | © 2017 Elsevier Inc. All rights reserved. | - |
dc.source.uri | http://dx.doi.org/10.1016/j.jinorgbio.2017.07.033 | - |
dc.subject | Hydroxamic Acids | - |
dc.subject | Macrocycles | - |
dc.subject | Metal-templated synthesis | - |
dc.subject | Siderophores | - |
dc.subject | Iron(III) | - |
dc.title | Dimeric and trimeric homo- and heteroleptic hydroxamic acid macrocycles formed using mixed-ligand Fe(III)-based metal-templated synthesis | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1016/j.jinorgbio.2017.07.033 | - |
dc.relation.grant | http://purl.org/au-research/grants/arc/DP140100092 | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Tieu, W. [0000-0002-7161-4152] | - |
Appears in Collections: | Aurora harvest 4 Molecular and Biomedical Science publications |
Files in This Item:
There are no files associated with this item.
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.