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The review presents specific interactions that occur in complexes of Cu(ll) ions with peptides composed only of amino acids with nonco-ordinating side chains. Three classes of such peptides are discussed. The first type (NSFRY analogues) is characterised by the presence of a specific combination of bulky and aromatic residues, leading to a formation of multiple weak interactions around Cu(II) that result in an extremely high stability of complexes. The second class is composed of complexes of vasopressins and oxytocins, achieving superstability through a pre-conformation in the peptide molecule. The third group are oligopeptides containing one or two proline residues. These peptides form exotic macrochelate loops with Cu(ll) in a result of the break-point effect of Pro residues. Particular emphasis in the review was given to stability constants of complexes, compared to oligoglycine or oligoalanine peptides.
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p.467-476,fig.
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- University of Wroclaw, F.Joliot-Curie 14, 50-383 Wroclaw, Poland
autor
autor
Bibliografia
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- 5. Hay, K.W., Hassan, M.M. & You-Quan, C. (1993) Kinetic and thermodynamic studies of the coppeKII) and nickel(II) complexes of gly- cylglycyl-I^histidine. J. Inorg. Biochem. 52, 17-25.
- 6. Sóvágó, I. (1990) Metal complexes of peptides and their derivatives; in Biocoordination Chemistry: Coordination Equilibra in Biologically Active Systems (Burger, K., ed.) pp. 135-184, Ellis Horwood, New York, Ix>ndon, Toronto, Sydney, Tokyo, Singapore.
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- 10. Decock-Le Reverend, B., Andrianarijaona, L., Livera, C., Pettit, L.D., Steel, I. & Kozlowski, H. (1986) A potentiometric and spectroscopic study of the interaction of the N terminal tetrapeptide fragment of fibrinopeptide A with Cu11 and Ni". J. Chem. Soc. Dalton Trans. 2221-2226.
- 11. Bal, W., Kozlowski, H., Kupryszewski, G., Mackiewicz, Z., Pettit, L.D. & Robbins, H. (1993) Complexes of Cu(II) with Asn-Ser-Phe- Arg-Tyr-NH2: An example of metal ion-promoted conformational organization which results in exceptionally high complex stability. J. Inorg. Biochem. 52, 79-87.
- 12. Czarnecki, J.J. & Margerum, D.W. (1977) Circular dichroism of copper and nickel tetra- and pentapeptide complexes. Inorg. Chem. 16, 1997-2003.
- 13. Yamauchi, O. & Odani, A. (1985) Structure- stability relationship in ternary copper(II) complexes involving aromatic amines and tyrosine or related amino acids. Intramolecular aromatic ring stacking and its regulation through tyrosine phosphorylation. J. Am. Chem. Soc. 107. 5938-5945.
- 14. Liang, G., Tribolet, R. & Sigel, H. (1989) Influence of dioxanc on the extent of intramolecular hydrophobic ligand-ligand interactions in the binary Cu2+ 1:2 complexes of L-leucinate, L-valinate and L-norvalinate. Inorg. Chim. Acta 155, 273-280.
- 15. Xiao. L., Jouini, M., Fan, B.T. & Lapluye, G. (1990) Potentiometric, calorimetric and spectroscopic study of complexation between cop- per(II), nickel(II), and L,L-dipeptides containing weakly or non-co-ordinating side chains. J. Chem. Soc. Dalton Trans. 1137-1146.
- 16. Pettit, L.D., Pyburn, S.I., Decock-I^ Reverend, B. & Lebkiri, A. (1989) The interaction of Cu(II) with Phe-Phe-Ser-Asp-Lys and other peptides containing the Phe-Phe sub-unit. Inorg. Chim. Acta 164, 235-238.
- 17. Radomska, B. & Kiss, T. (.1990) CopperUI) complexes of tyrosine-containing di- and tri- peptides. J. Coord. Chem. 21, 81-85.
- 18. Formicka-Kozłowska, G., Pettit, L.D., Steel, I. & Livera. C.E. (1985) A potentiometric and spectroscopic study of the proton and cop- peri II) complexes of methionine enkephalin and some related ligands. J. Inorg. Biochem. 24, 299-307.
- 19. Kozlowski, H. (1978) Spectroscopic and magnetic resonance studies on Ni(II), Cu(II) and Pd(II) complexes with Gly-Leu-Tyr and Tyr- Gly-Gly tri peptides. Inorg. Chim. Acta 31, 135-140.
- 20. Kiss, T. (1987) Copper<II) complexes of tyrosine-containing tripeptides. J. Chem. Soc. Dalton Trans. 1263-1265.
- 21. Bal, W., Dyba, M.. Kasprzykowski, F., Kozlowski. H., Latajka, R., Łankiewicz, L. & Mackiewicz, Z. (1996) Exceptionally high stability of Cu complexes with pentapeptide fragment of atrial natriuretic factor. Looking for reason; in NATO Advanced Study Institute, Cytotoxic, Mutagenic and Carcinogenic Potential of Heavy Metals Related to Human Environment. Przesieka, Poland, Book of Abstracts, pp. 165-166.
- 22. Kozłowski, H., Radomska, B., Kupryszewski, G., Lammek. B., Livera, C., Pettit, L.D. & Pyburn, S. (1989) The unusual co-ordination ability of vasopressin-like peptides; Potentiometric and spectroscopic studies of some copper(II) and nickel(II) complexes. J. Chem. Soc. Dalton Trans. 173-177.
- 23. Bal, W., Kozłowski, IL, Lammek, B., Pettit, L.D. & Rolka, K. (1992) Potentiometric and spectroscopic studies of the Cu(II) complexes of Ala-Arg -vasopressin and oxytocin: Two vasopressin-like peptides. J. Iiwrg. Biochem. 45, 193-202.
- 24. Kozłowski, H. (1983) Specific function of proline residue in metal-peptide systems. Proceedings of the 9th Conference on Coordination Chemistry, pp. 201-205, Smolenice, Bratislava, ĆSSR,.
- 25. Kozłowski. II., Bezer, M., Pettit, L.D., Ba tai Ile, M. & Hecquet, B. (1983) Coordination abilities of tetrapeptides containing proline and tyrosine — a spectrophotometry and potentiometric study. J. Inorg. Biochem. 18, 231-240.
- 26. Pettit, L.D., Steel, I., Hartrodt, B., Neubert, K., Rekowski, P. & Kupryszewski, G. (1984) The coordination of copper(II) with (3-caso- morphin and its fragments. J. Iriorg. Bio- chem. 22, 155-163.
- 27. Pettit, L.D., Steel, I., Kowalik, T., Kozłowski, H. & Bataille, M. (1985) Specific binding of the tyrosine residue in copper (II) complexes of Tyr-Pro-Gly-Tyr and Tyr-Gly-Pro-Tyr. J. Chem. Soc. Dalton Trans. 1201-1205.
- 28. Formicka-Kozłowska, G., Konopińska, D.t Kozłowski, H. & Decock-Le Reverand, B. (1983) Copperill) complexes with canine tuftsinyltuflsin octapeptide. A novel mode of metal-peptide coordination. Inorg. Chim. Ada. 78, U7-L49.
- 29. Formicka-Kozłowska, G., Kozłowski, H., Siemion, I.Z., Sobczyk, K. & Nawrocka, E. (1981) Copper (II) interaction with proline- containing tetrapeptides. J. Inorg. Biochem. 15, 201-212.
- 30. Bezer, M., Pettit, L.D., Steel, 1., Bataille, M., Djemil, S. & Kozłowski, H. (1984) CopperdI) interaction with tetrapeptides containing proline and phenylalanine. A potentiometric and spectrophotometric study. J. Inorg. Biochem. 20. 13-21.
- 31. Livera, C., Pettit, L.D., Bataille, M., Krembel, J., Bal, W. & Kozłowski, H. (1988) Copper(II) complexes with some tetrapeptides containing the "break-point" prolyl residue in the third position. J. Chem. Soc. Dalton Trans. 1357-1360.
- 32. Pettit, L.D., Livera, C., Steel, 1., Bataille, M., Cardon, C. & Formicka-Kozłowska, G. (1987) The influence of the proline residue on the co-ordination of Cu(II) to peptides containing -Pro- and -Pro-Pro- sub-units. Polyhedron 6, 45-52.
- 33. Pettit, L.D., Bal, W., Bataille, M., Cardon, C., Kozłowski, H., I/Cseinc-Delstanche, M., Py- burn, S. & Scozzafava, A. (1991) A thermodynamic and spectroscopic study of the complexes of the undecapeptide Substance P, of its N-terminal fragment and of model pen- tapeptides containing two prolyl residues with copper ions. J. Chem. Soc. Dalton Trans. 1651-1656.
- 34. Kozłowski, H., Formicka-Kozłowska, G., Pettit, L.D. & Steel, I. (1986) Can coppeKII) ions biologicaly activate small peptide molecules; in Frontiers in Bioinorganic Chemistry (Xavier, A.V., cd.) pp. 668-675, VCH, Wein- heim.
- 35. Schwederski, B.E., Basile-D'Alessandro. F., Dickson, P.N., Lee, H I)., Raycheba, eJ.M.T. & Margerum, D.W. (1989) Methyl group steric effects on the kinetics of the copper(II)-tripep- tide reactions with triethylenetetramine. Inorg. Chem. 28, 3477-3480.
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Bibliografia
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