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Synthesis and characterization of metal binding pseudotripeptides
Author(s) -
Kuenzel Sebastian,
Pretzel David,
Andert Janet,
Beck Kirsten,
Reissmann Siegmund
Publication year - 2003
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.468
Subject(s) - chemistry , metal , transition metal , peptide , selectivity , catalysis , combinatorial chemistry , chelation , stereochemistry , amino acid , organic chemistry , biochemistry
Abstract Metal complexes with peptide or pseudopeptide type ligands can serve as good model compounds for a deeper understanding of enzymatic catalysis, but ligands with a high selectivity for different transition metal cations are hard to find due to the rather flexible nature of peptides. Since such ligands would be the sine qua non condition for the synthesis of heterodinuclear peptide metal complexes with catalytic activity, the search for small, affine and selective metal chelating sequences is of interest. Using four different amino acids (His, Lys, Asp, Glu) a set of 16 pseudotripeptides of the common structure Bz‐AS 1 ‐Sar‐AS 2 ‐NH 2 has been synthesized, purified and characterized by mass spectrometry and 1 H‐NMR. Their ability to form metal complexes has been investigated leading to short motifs capable of selectively binding only one or two transition metal cations with high affinity. As expected, the complexation of transition metal cations by pseudotripeptides is strongly dependent not only on the amino acid composition, but also on the sequence with regard to the stability of the resulting complexes, as well as the selectivity of the ligands towards Cu 2+ , Co 2+ , Ni 2+ , Zn 2+ and Mn 2+ . Copyright © 2003 European Peptide Society and John Wiley & Sons, Ltd.