Multinuclear NMR and potentiometric study on tautomerism during protonation and zinc(II) complex formation of some imidazole-containing peptide derivatives

T. Gajda, Bernard Henry, Jean Jacques Delpuech

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Abstract

The acid-base properties and zinc(II) complexes of glycylhistamine, sarcosylhistamine, carcinine and carnosine have been studied by potentiometric, 13C and 14N NMR methods. Macroscopic species for the three states of protonation (LH2 2+, LH+, L) and the corresponding microspecies involving three protonation sites (terminal amino, N-1 and -3 imidazole nitrogens) are quantitatively estimated for the metal-free ligands. Zinc(II) complexation is shown to reverse the tautomeric preference between 1- and 3-H tautomeric forms of the imidazole ring (in LH+ and L), as compared to the free ligands where the 1-H tautomer is predominant.

Original languageEnglish
Pages (from-to)157-164
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number1
Publication statusPublished - 1994

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Protonation
Zinc
Nuclear magnetic resonance
Carnosine
Ligands
Derivatives
Peptides
Complexation
Nitrogen
Metals
Acids
imidazole
glycylhistamine
carcinine

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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AB - The acid-base properties and zinc(II) complexes of glycylhistamine, sarcosylhistamine, carcinine and carnosine have been studied by potentiometric, 13C and 14N NMR methods. Macroscopic species for the three states of protonation (LH2 2+, LH+, L) and the corresponding microspecies involving three protonation sites (terminal amino, N-1 and -3 imidazole nitrogens) are quantitatively estimated for the metal-free ligands. Zinc(II) complexation is shown to reverse the tautomeric preference between 1- and 3-H tautomeric forms of the imidazole ring (in LH+ and L), as compared to the free ligands where the 1-H tautomer is predominant.

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