Studies on transition-metal-peptide complexes. Part 9. Copper(II) complexes of tripeptides containing histidine

E. Farkas, I. Sóvágó, T. Kiss, Arthur Gergely

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Abstract

Copper(II) complexes of the histidine-containing tripeptides glyclyl-L-histidylglycine (GlyHisGly), glycylglycyl-L-histidine (GlyGlyHis), and L-pyroglutamyl-L-histidyl-L-prolinamide (trf), and the dipeptide L-pyroglutamyl-L-histidine methyl ester (pghme), have been studied by pH-metric and spectrophotometric methods. It was found that, similarly as for glycyl-L-histidine (GlyHis), GlyHisGly forms a complex [CuAH-1], but bis complexes are also formed in low concentration. For GlyGlyHis, only the highly stable species [CuAH-2]- is formed. A complex [CuAH-2]- is also formed with trf and pghme which indicates that the prolinamide side-chain in trf does not take part in the co-ordination. The sequence of deprotonation of the N1H group of the imidazole side-chain is as follows: GlyHisGly > GlyHis > pghme > trf > GlyGlyHis.

Original languageEnglish
Pages (from-to)611-614
Number of pages4
JournalJournal of the Chemical Society, Dalton Transactions
Issue number4
DOIs
Publication statusPublished - 1984

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diglycyl-histidine
histidylglycine
Histidine
glycylhistidine
Transition metals
Copper
Peptides
Deprotonation
Dipeptides
histidine methyl ester

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Studies on transition-metal-peptide complexes. Part 9. Copper(II) complexes of tripeptides containing histidine",
abstract = "Copper(II) complexes of the histidine-containing tripeptides glyclyl-L-histidylglycine (GlyHisGly), glycylglycyl-L-histidine (GlyGlyHis), and L-pyroglutamyl-L-histidyl-L-prolinamide (trf), and the dipeptide L-pyroglutamyl-L-histidine methyl ester (pghme), have been studied by pH-metric and spectrophotometric methods. It was found that, similarly as for glycyl-L-histidine (GlyHis), GlyHisGly forms a complex [CuAH-1], but bis complexes are also formed in low concentration. For GlyGlyHis, only the highly stable species [CuAH-2]- is formed. A complex [CuAH-2]- is also formed with trf and pghme which indicates that the prolinamide side-chain in trf does not take part in the co-ordination. The sequence of deprotonation of the N1H group of the imidazole side-chain is as follows: GlyHisGly > GlyHis > pghme > trf > GlyGlyHis.",
author = "E. Farkas and I. S{\'o}v{\'a}g{\'o} and T. Kiss and Arthur Gergely",
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TY - JOUR

T1 - Studies on transition-metal-peptide complexes. Part 9. Copper(II) complexes of tripeptides containing histidine

AU - Farkas, E.

AU - Sóvágó, I.

AU - Kiss, T.

AU - Gergely, Arthur

PY - 1984

Y1 - 1984

N2 - Copper(II) complexes of the histidine-containing tripeptides glyclyl-L-histidylglycine (GlyHisGly), glycylglycyl-L-histidine (GlyGlyHis), and L-pyroglutamyl-L-histidyl-L-prolinamide (trf), and the dipeptide L-pyroglutamyl-L-histidine methyl ester (pghme), have been studied by pH-metric and spectrophotometric methods. It was found that, similarly as for glycyl-L-histidine (GlyHis), GlyHisGly forms a complex [CuAH-1], but bis complexes are also formed in low concentration. For GlyGlyHis, only the highly stable species [CuAH-2]- is formed. A complex [CuAH-2]- is also formed with trf and pghme which indicates that the prolinamide side-chain in trf does not take part in the co-ordination. The sequence of deprotonation of the N1H group of the imidazole side-chain is as follows: GlyHisGly > GlyHis > pghme > trf > GlyGlyHis.

AB - Copper(II) complexes of the histidine-containing tripeptides glyclyl-L-histidylglycine (GlyHisGly), glycylglycyl-L-histidine (GlyGlyHis), and L-pyroglutamyl-L-histidyl-L-prolinamide (trf), and the dipeptide L-pyroglutamyl-L-histidine methyl ester (pghme), have been studied by pH-metric and spectrophotometric methods. It was found that, similarly as for glycyl-L-histidine (GlyHis), GlyHisGly forms a complex [CuAH-1], but bis complexes are also formed in low concentration. For GlyGlyHis, only the highly stable species [CuAH-2]- is formed. A complex [CuAH-2]- is also formed with trf and pghme which indicates that the prolinamide side-chain in trf does not take part in the co-ordination. The sequence of deprotonation of the N1H group of the imidazole side-chain is as follows: GlyHisGly > GlyHis > pghme > trf > GlyGlyHis.

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