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Synthesis And Copper(II)-Complexation Properties Of An Unusual Macrocyclic Structure Containing α/β-Amino Acids And Anomeric Sugar β-Amino Acid

Anne-Sophie Felten, Anne-Sophie Felten, N. Pellegrini-Moïse, N. Pellegrini-Moïse, Katalin Selmeczi, Katalin Selmeczi, B. Henry, B. Henry, Yves Chapleur, Yves Chapleur
Published 2013 · Chemistry

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A 16-membered macrocycle containing histidine, β-alanine, and an anomeric sugar β-amino acid was synthesised using a stepwise procedure starting from an exo-glycal derivative. This new macrocyclic structure contains an unusual carbonic carbamic anhydride moiety that was spontaneously formed upon saponification of the C-terminus ester group by attack of the resulting carboxylate group on the N-terminal benzyloxycarbonyl protecting group. This macrocyclic ligand formed a 1:1 complex with copper(II) ions in aqueous solution at basic pH. A structural study of this complex in solution was undertaken by UV/Vis, and paramagnetic 1H and 13C NMR spectroscopy. These spectroscopic data strongly suggest a {3 × Namide, NIm} equatorial donor set around the copper(II) ion, the fourth amide nitrogen being inaccessible for coordination, probably due to the rigid structure imposed by the sugar unit and the anhydride moiety.
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