Silver complexes of peptidomimetic polyazapyridinophanes. The influence of the bonding cavity size and the nature of side chains |
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Authors: | Alfonso Ignacio Burguete Isabel Luis Santiago V Miravet Juan F Seliger Piotr Tomal Ewa |
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Affiliation: | Department of Inorganic and Organic Chemistry, UAMOA, University Jaume I/CSIC, 12071 Castellón, Spain. |
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Abstract: | Several peptidomimetic macrocycles containing a pyridine spacer and ring sizes ranging from 15 to 17 have been efficiently synthesized starting from valine and phenylalanine. The complexes formed have been investigated by potentiometry and NMR. Log K values show that phenylalanine derivatives are consistently more stable than valine derivatives , whilst macrocycles with ring sizes of 16 members are the most appropriate for the complexation. The NMR data, in combination with molecular modeling, allow rationalization of the structure of the complexes formed and the participation of the aromatic rings from the side chain of phenylalanine in pi-Ag+ interactions to be discarded. |
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