NDLI: Synthesis and Investigation of a Chiral Enterobactin Analogue Based on a Macrocyclic Peptide Scaffold

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Synthesis and Investigation of a Chiral Enterobactin Analogue Based on a Macrocyclic Peptide Scaffold

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Haberhauer, Gebhard Pintér, Aron
Description	Author Affiliation: Pintér A ( Institut für Organische Chemie, Fachbereich Chemie, Universität Duisburg-Essen, Universitätsstrasse 7, 45117 Essen, Germany.)
Abstract	A chiral $C_{3}-symmetric$ enterobactin analogue (1) has been synthesized by attachment of three 2,3-dihydroxybenzoyl units to a chiral oxazole-containing macrocyclic peptide scaffold. Complex formation kinetics and stoichiometry with various metal ions were investigated by spectrophotometric methods. In the cases of $Al^{III},$ $In^{III}$ and $Fe^{III}$ complexes, UV absorption and CD kinetics showed nonlinearity, which results from slow conformational changes of the octahedral complexes. Virtual binding constants were determined from UV absorption data and showed selective binding of $Ga^{III}$ in preference to $Fe^{III},$ by two orders of magnitude. CD spectroscopy revealed highly diastereoselective binding of $Al^{III},$ $Ga^{III},$ $In^{III},$ $Fe^{III}$ and $Ge^{IV}$ ions at room temperature, corresponding to the helical chirality opposite to that of the analogous enterobactin complexes. Ab initio calculations confirmed the energetic stabilization of the Λ isomers relative to the Δ isomers.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	35
Volume Number	14
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2008-01-01
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Enterobactin Analogs & Derivatives Peptides, Cyclic Chemistry Kinetics Macrocyclic Compounds Metals, Heavy Models, Molecular Molecular Conformation Spectrum Analysis Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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