Lodyga-Chruscinska, Elzbieta and Micera, Giovanni and Sanna, Daniele and Olczak, Jacek and Zabrocki, Janusz and Kozlowski, Henryk and Chruscinski, Longin (1999) Effect of the tetrazole cis-amide bond surrogate on the complexing ability of some enkephalin analogues toward Cu(II) ions. Journal of Inorganic Biochemistry, Vol. 76 (1). ISSN 0162-0134. Article.
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A study of the effect of the tetrazole moiety, a cis-amide bond surrogate, on the Cu(II) coordinating properties of oligopeptides is reported. The insertion of the tetrazole moiety ψ(CN4) into the peptide sequence of [Leu5]enkephalin considerably changes the coordination ability of the ligand. Potentiometric and spectroscopic results indicate that if the tetrazole moiety is in a suitable position in the peptide chain, i.e. if it follows the third residue, an unusual stable CuH−1L species involving 4N coordination is formed in the physiological pH region. The tetrazole ψ(CN4) ring provides one of these nitrogens. The data indicate that Cu(II) ions are strongly trapped inside a bent peptide backbone. However, the coordination mode involving the tetrazole ring nitrogen does not prevent the hydrolysis process under strongly basic conditions.
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