Transition-metal complexes of carcinine, a peptide-type derivative of histamine

T. Gajda, Bernard Henry, Jean Jacques Delpuech

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The acid-base properties and copper(II), nickel(II) and cobalt(II) complexes of carcinine {3-amino-N-[2-(imidazol-4-yl)ethyl]propanamide} and of N-tert-butoxycarbonylcarcinine have been studied at 25°C by pH-metric, spectrophotometric and, in part, 1H NMR and EPR methods, and compared to those of histidine-containing dipeptides. Complexes of the type M(HL), ML and ML2 (charges omitted) are found in the cobalt(II) and nickel(II) systems, with the additional presence of ML2H-1 for the latter system. Copper(II) forms CuLn (n ≤ 4) complexes with N-tert-butoxycarbonylcarcinine molecules acting as monodentate ligands. The copper(II)-carcinine system in the range pH 3-9 shows the expected series of 1: 1 complexes, more or less deprotonated depending on the pH, of type Cu(HL), CuL and CuLH-1, and, for an excess of ligand, the unusual 1: 4 complex CuL4H2 involving four N(3) inidazole nitrogens equatorially co-ordinated. At higher pH (> 9) the monomeric CuLH-2 and polynuclear Cu4L4H-8 complexes are formed depending on the total concentration. The tetrameric species probably involves co-ordination of deprotonated N(1)-pyrrole nitrogens, with consequent formation of imidazolate bridges. The co-ordination ability of the peptide nitrogen in histidyl- and histamine-peptides is shown to depend on the size of the chelate rings formed and the existence of a neighbouring carboxyl group in the ligand.

Original languageEnglish
Pages (from-to)2313-2319
Number of pages7
JournalJournal of the Chemical Society, Dalton Transactions
Issue number15
DOIs
Publication statusPublished - 1992

Fingerprint

Coordination Complexes
Histamine
Transition metals
Copper
Nitrogen
Ligands
Cobalt
Nickel
Derivatives
Peptides
Pyrroles
Dipeptides
Histidine
Paramagnetic resonance
Nuclear magnetic resonance
Molecules
Acids
carcinine

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Transition-metal complexes of carcinine, a peptide-type derivative of histamine. / Gajda, T.; Henry, Bernard; Delpuech, Jean Jacques.

In: Journal of the Chemical Society, Dalton Transactions, No. 15, 1992, p. 2313-2319.

Research output: Contribution to journalArticle

@article{5af0ce49138d407db98c37497222a568,
title = "Transition-metal complexes of carcinine, a peptide-type derivative of histamine",
abstract = "The acid-base properties and copper(II), nickel(II) and cobalt(II) complexes of carcinine {3-amino-N-[2-(imidazol-4-yl)ethyl]propanamide} and of N-tert-butoxycarbonylcarcinine have been studied at 25°C by pH-metric, spectrophotometric and, in part, 1H NMR and EPR methods, and compared to those of histidine-containing dipeptides. Complexes of the type M(HL), ML and ML2 (charges omitted) are found in the cobalt(II) and nickel(II) systems, with the additional presence of ML2H-1 for the latter system. Copper(II) forms CuLn (n ≤ 4) complexes with N-tert-butoxycarbonylcarcinine molecules acting as monodentate ligands. The copper(II)-carcinine system in the range pH 3-9 shows the expected series of 1: 1 complexes, more or less deprotonated depending on the pH, of type Cu(HL), CuL and CuLH-1, and, for an excess of ligand, the unusual 1: 4 complex CuL4H2 involving four N(3) inidazole nitrogens equatorially co-ordinated. At higher pH (> 9) the monomeric CuLH-2 and polynuclear Cu4L4H-8 complexes are formed depending on the total concentration. The tetrameric species probably involves co-ordination of deprotonated N(1)-pyrrole nitrogens, with consequent formation of imidazolate bridges. The co-ordination ability of the peptide nitrogen in histidyl- and histamine-peptides is shown to depend on the size of the chelate rings formed and the existence of a neighbouring carboxyl group in the ligand.",
author = "T. Gajda and Bernard Henry and Delpuech, {Jean Jacques}",
year = "1992",
doi = "10.1039/DT9920002313",
language = "English",
pages = "2313--2319",
journal = "Dalton Transactions",
issn = "1472-7773",
publisher = "Royal Society of Chemistry",
number = "15",

}

TY - JOUR

T1 - Transition-metal complexes of carcinine, a peptide-type derivative of histamine

AU - Gajda, T.

AU - Henry, Bernard

AU - Delpuech, Jean Jacques

PY - 1992

Y1 - 1992

N2 - The acid-base properties and copper(II), nickel(II) and cobalt(II) complexes of carcinine {3-amino-N-[2-(imidazol-4-yl)ethyl]propanamide} and of N-tert-butoxycarbonylcarcinine have been studied at 25°C by pH-metric, spectrophotometric and, in part, 1H NMR and EPR methods, and compared to those of histidine-containing dipeptides. Complexes of the type M(HL), ML and ML2 (charges omitted) are found in the cobalt(II) and nickel(II) systems, with the additional presence of ML2H-1 for the latter system. Copper(II) forms CuLn (n ≤ 4) complexes with N-tert-butoxycarbonylcarcinine molecules acting as monodentate ligands. The copper(II)-carcinine system in the range pH 3-9 shows the expected series of 1: 1 complexes, more or less deprotonated depending on the pH, of type Cu(HL), CuL and CuLH-1, and, for an excess of ligand, the unusual 1: 4 complex CuL4H2 involving four N(3) inidazole nitrogens equatorially co-ordinated. At higher pH (> 9) the monomeric CuLH-2 and polynuclear Cu4L4H-8 complexes are formed depending on the total concentration. The tetrameric species probably involves co-ordination of deprotonated N(1)-pyrrole nitrogens, with consequent formation of imidazolate bridges. The co-ordination ability of the peptide nitrogen in histidyl- and histamine-peptides is shown to depend on the size of the chelate rings formed and the existence of a neighbouring carboxyl group in the ligand.

AB - The acid-base properties and copper(II), nickel(II) and cobalt(II) complexes of carcinine {3-amino-N-[2-(imidazol-4-yl)ethyl]propanamide} and of N-tert-butoxycarbonylcarcinine have been studied at 25°C by pH-metric, spectrophotometric and, in part, 1H NMR and EPR methods, and compared to those of histidine-containing dipeptides. Complexes of the type M(HL), ML and ML2 (charges omitted) are found in the cobalt(II) and nickel(II) systems, with the additional presence of ML2H-1 for the latter system. Copper(II) forms CuLn (n ≤ 4) complexes with N-tert-butoxycarbonylcarcinine molecules acting as monodentate ligands. The copper(II)-carcinine system in the range pH 3-9 shows the expected series of 1: 1 complexes, more or less deprotonated depending on the pH, of type Cu(HL), CuL and CuLH-1, and, for an excess of ligand, the unusual 1: 4 complex CuL4H2 involving four N(3) inidazole nitrogens equatorially co-ordinated. At higher pH (> 9) the monomeric CuLH-2 and polynuclear Cu4L4H-8 complexes are formed depending on the total concentration. The tetrameric species probably involves co-ordination of deprotonated N(1)-pyrrole nitrogens, with consequent formation of imidazolate bridges. The co-ordination ability of the peptide nitrogen in histidyl- and histamine-peptides is shown to depend on the size of the chelate rings formed and the existence of a neighbouring carboxyl group in the ligand.

UR - http://www.scopus.com/inward/record.url?scp=37049086859&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=37049086859&partnerID=8YFLogxK

U2 - 10.1039/DT9920002313

DO - 10.1039/DT9920002313

M3 - Article

AN - SCOPUS:37049086859

SP - 2313

EP - 2319

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1472-7773

IS - 15

ER -