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An enantiomerically pure siderophore type ligand for the diastereoselective 1 : 1 complexation of lanthanide(III) ions

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Author(s): Markus Albrecht | Olga Osetska | Thomas Abel | Gebhard Haberhauer | Eva Ziegler

Journal: Beilstein Journal of Organic Chemistry
ISSN 1860-5397

Volume: 5;
Issue: 1;
Start page: 78;
Date: 2009;
Original page

Keywords: CD spectroscopy | enterobactin | lanthanide | macrocycles | molecular modeling

ABSTRACT
A facile synthesis of a highly preorganized tripodal enterobactine-type ligand 1a-H3 consisting of a chiral C3-symmetric macrocyclic peptide and three tridentate 2-amido-8-hydroxyquinoline coordinating units is presented. Complex formation with various metal ions (Al3+, Ga3+, Fe3+, La3+ and Eu3+) was investigated by spectrophotometric methods. Only in the case of La3+ and Eu3+ were well defined 1 : 1 complexes formed. On the basis of CD spectroscopy and DFT calculations the configuration at the metal centre of the La3+ complex was determined to show Λ helicity. The coordination compounds [(1a)Ln] presented should be prototypes for further lanthanide(III) complexes with an enterobactine analogue binding situation.

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