Journal
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
Volume 21, Issue 5, Pages 349-358Publisher
WILEY
DOI: 10.1002/poc.1328
Keywords
alpha/beta-tetrapeptides; solid phase synthesis; coordination; metal ions; electrospray-ionization mass spectrometry
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Thirty-four novel alpha/beta-tetrapeptides (1-34) have been prepared employing solid-phase and in-parallel synthetic protocols. alpha/beta-Tetrapeptides 1-34 were prepared by a combination of three a-amino acid residues (alanine (Ala), phenylalanine (Phe), and isoleucine (Ille)) with one beta-amino acid residue (beta(3)-homophenylglycine). The corresponding complexes of several selected alpha/beta-tetrapeptides with alkali, alkaline earth, and transition metals, [tP + M+], were evaluated using ion electrospray-ionization mass spectrometry (ESI-MS). According to the results from analysis of mixtures, we can conclude that the position of the beta-amino acid is determinant in the affinity toward different metal cations. Computational modeling (DFT, B3LYP 6-311++G) provided useful information regarding the most likely coordination sites of the metal ions on the receptor alpha/beta-tetrapeptide 12, HO2C-alpha-Phe-alpha-Phe-alpha-Ile-beta(3) -hPhg-NH2, as well as the conformational changes induced by the metal upon [tP + M+] complex formation. Copyright (C) 2008 John Wiley & Sons, Ltd.
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