Ferric ion sequestering agents. 15. Synthesis, solution chemistry, and electrochemistry of a new cationic analog of enterobactin

Rodgers, S. J.; Lee, Chi Woo; Ng, Chiu Yuen; Raymond, Kenneth N.

doi:10.1021/ic00257a030

Cited by 126 publications

(115 citation statements)

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“…2A) built on the robust tris(2-aminoethyl)amine (Tren) scaffold that retains integrity over a wide pH range ( Fig. S2) (22). TLC exhibits nearly identical adsorption and adhesion behavior to the natural CTC siderophore.…”

Section: Tris-23-dhba-d-lys-l-sermentioning

confidence: 99%

Adaptive synergy between catechol and lysine promotes wet adhesion by surface salt displacement

Maier

Rapp

Waite

et al. 2015

Science

589

588

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authors contributed equally to this work.One Sentence Summary: Siderophore-inspired, mussel foot protein mimetic adhesives resist oxidation and reveal a synergistic catechol-lysine interplay that enables wet adhesion to mineral surfaces Abstract: In physiological fluids and seawater, adhesion of synthetic polymers to solid surfaces is severely limited by high salt, pH, and hydration, yet these conditions have not deterred the evolution of effective adhesion by mussels. Mussel foot proteins provide insights about adhesive adaptations: notably, the abundance and proximity of catecholic Dopa (3,4-dihydroxyphenylalanine) and lysine residues hint at a synergistic interplay in adhesion. Certain siderophores-bacterial iron-chelators-consist of paired catechol and lysine functionalities thereby providing a convenient experimental platform to explore molecular synergies in bioadhesion. These siderophores and synthetic analogs exhibit robust adhesion (W adh ≥15mJ/m 2 )to mica in saline pH 3.5-7.5 and resist oxidation. The adjacent catechol-Lys placement provides a "1-2 punch", whereby Lys evicts hydrated cations from the mineral surface, allowing catechol binding to underlying oxides.

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Section: Tris-23-dhba-d-lys-l-sermentioning

confidence: 99%

Adaptive synergy between catechol and lysine promotes wet adhesion by surface salt displacement

Maier

Rapp

Waite

et al. 2015

Science

589

588

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“…The ΔG tr values (−23.2 kJ mol −1 for acetonitrile) have been tabulated by IUPAC. 43 (6) The reduction potentials for the ferric complexes [Fe III 44 The ligands built on a serine-trilactone scaffold form ferric complexes with higher reduction potentials than the equivalent TREN-based compounds. This trend has been observed earlier with hydroxypyridonate enterobactinanalogs.…”

Section: Electrochemical Characterization Of Ferric Salicylate Complexesmentioning

confidence: 99%

Enterobactin Protonation and Iron Release: Structural Characterization of the Salicylate Coordination Shift in Ferric Enterobactin¹

et al. 2006

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The siderophore enterobactin (Ent) is produced by many species of enteric bacteria to mediate iron uptake. This iron scavenger can be reincorporated by the bacteria as the ferric complex [Fe III (Ent)] 3-and is subsequently hydrolyzed by an esterase to facilitate intracellular iron release. Recent literature reports on altered protein recognition and binding of modified enterobactin increase the significance of understanding the structural features and solution chemistry of ferric enterobactin. The structure of the neutral protonated ferric enterobactin complex [Fe III (H 3 (14) Å 2 ). 1 H NMR spectroscopy was used to monitor the amide bond rotation between the catecholate and salicylate geometries using the gallic complexes of enterobactin; [Ga III (Ent)] 3-and [Ga III (H 3 Ent)] 0 . The ferric salicylate complexes display quasi-reversible reduction potentials from −89 mV to −551 mV (relative to the normal hydrogen electrode NHE) which supports the feasibility of a low pH iron release mechanism facilitated by biological reductants. Keywords

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“…79 The amide proton forms a hydrogen bond to the internal catecholate oxygen atom. Due to this fixation, flexible tripodal catecholamides (like trencam) 80 are ideal for the binding of metal ions. In case of catechol imines the situation is different.…”

Section: Tripodal Triscatechol Ligands For the Formation Of Mononuclementioning

confidence: 99%

Symmetry Driven Self-Assembly of Metallo-Supramolecular Architectures

Albrecht¹,

Fröhlich²

2007

Bulletin of the Chemical Society of Japan

111

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The self-assembly of well-defined metallosupramolecular aggregates highly depends on the symmetry of the ligands as well as of the metals. Approaches in which symmetry considerations allow the stepwise-''hierarchical''-assembly of helicate-type complexes from very simple catechol derivatives are described. In addition helicates and meso-helicates are stereoselectively obtained by the use of linear ligands possessing the relevant symmetry element for the formation of either diastereomer (even-odd principle). In case of helicates, this allows the preparation of enantiomerically pure complexes. Finally, the self-assembly of tetrahedral M 4 L 4 complexes is described using either constrained flexible or highly predisposed rigid ligands.

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Ferric ion sequestering agents. 15. Synthesis, solution chemistry, and electrochemistry of a new cationic analog of enterobactin

Cited by 126 publications

References 0 publications

Adaptive synergy between catechol and lysine promotes wet adhesion by surface salt displacement

Adaptive synergy between catechol and lysine promotes wet adhesion by surface salt displacement

Enterobactin Protonation and Iron Release: Structural Characterization of the Salicylate Coordination Shift in Ferric Enterobactin¹

Symmetry Driven Self-Assembly of Metallo-Supramolecular Architectures

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Ferric ion sequestering agents. 15. Synthesis, solution chemistry, and electrochemistry of a new cationic analog of enterobactin

Cited by 126 publications

References 0 publications

Adaptive synergy between catechol and lysine promotes wet adhesion by surface salt displacement

Adaptive synergy between catechol and lysine promotes wet adhesion by surface salt displacement

Enterobactin Protonation and Iron Release: Structural Characterization of the Salicylate Coordination Shift in Ferric Enterobactin1

Symmetry Driven Self-Assembly of Metallo-Supramolecular Architectures

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Enterobactin Protonation and Iron Release: Structural Characterization of the Salicylate Coordination Shift in Ferric Enterobactin¹