How Many O-Donor Groups in Enterobactin Does It Take to Bind a Metal Cation?

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Title
How Many O-Donor Groups in Enterobactin Does It Take to Bind a Metal Cation?
Author(s)
Todor Baramov; Bianca Schmid; Ho Ryu; Jinhoon Jeong; Karlijn Keijzer; Leonard von Eckardstein; Mu-Hyun Baik; Roderich D. Sessmuth
Publication Date
2019-05
Journal
CHEMISTRY-A EUROPEAN JOURNAL, v.25, no.28, pp.6955 - 6962
Publisher
WILEY-V C H VERLAG GMBH
Abstract
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim The E. coli siderophore enterobactin, the strongest Fe III chelator known to date, forms hexacoordinate complexes with Si IV , Ge IV , and Ti IV . Synthetic protocols have been developed to prepare non-symmetric enterobactin analogues with varying denticities. Various benzoic acid residues were coupled to the macrocyclic lactone to afford a diverse library of ligands. These enterobactin analogues were bound to Si IV , Ge IV , and Ti IV , and the complexes were investigated through experimental and computational techniques. The binding behavior of the synthesized chelators enabled assessment of the contribution of each of the phenolic hydroxy groups in enterobactin to metal-ion complexation. It was found that at least four O-donors are needed for enterobactin derivatives to act as metal binders. Density functional theory calculations indicate that the strong binding behavior of enterobactin can be ascribed to a diminished translational entropy penalty, a common feature of the chelate effect, coupled with the structural arrangement of the three catechol moieties, which allows the triseryl base to be installed without distorting the preferred local metal-binding geometry of the catecholate ligands
URI
https://pr.ibs.re.kr/handle/8788114/5971
ISSN
0947-6539
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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