The role of terminal amino group and histidine at the fourth position in the metal ion binding of oligopeptides revisited: Copper(II) and nickel(II) complexes of glycyl-glycyl-glycyl-histamine and its N-Boc protected derivative

Amino acid-based tweezers: The role of turn-like conformation in the binding of copper(II)

“…It was found that histidine side-chain competes for Cu(II) binding with the amino terminus upon the increase of pH, although amino group is a possible binding site at any pH value. One of the recent studies explored the role of N-terminal amino group and the imidazole moiety of histamine placed at the fourth position (pseudotetrapeptide glycylglycyl-glycyl-histamine, GGGHa and its N-Boc protected derivative, Boc-GGGHa) in the Cu(II) binding [7]. Higher stabilities of ML complexes were found for GGGHa compared with protected derivative Boc-GGGHa, supporting the importance of the N-terminal amino group for metal ion coordination.…”

Selective control of Cu(II) complex stability in histidine peptides by β-alanine

“…Depending on their relative position in the peptide chain, the N-terminal amine and the His imidazole can compete or cooperate as Cu(II) anchoring points [4,5]. The peptides containing His in position 3 (His-3) bind Cu(II) particularly effectively, due to the simultaneous formation of three chelate rings [2,3].…”

“…Previous research in this area was confined to main chain peptides. 4N, all-α-amino acid peptides contain three 5-membered rings (5,5,5). It was demonstrated that the introduction of the β-Ala residue, which forms a 6-membered ring, in various positions of the tetrapeptide chain affects the Cu(II) complex stability in the following manner: (5,5,5) ≥ (5,6,5) ≫ (5,5,6) > (6,5,5) [20].…”

Synthesis and Copper(II)‐Complexation Properties of an Unusual Macrocyclic Structure Containing α/β‐Amino Acids and Anomeric Sugar β‐Amino Acid

“…In particular, the significant role of the histidine residue in Cu II complexation has been widely reported 14–17. In connection with our previous work on sugar‐containing cyclic peptide derivatives and our research into the use of peptides as metal‐complexing agents,18–26 we became interested in the construction of macrocyclic structures made up of sugar β‐amino acids, and α‐ and β‐amino acids, in order to study their structures and their complexing properties.…”