METAL-COMPLEXES WITH MACROCYCLIC LIGANDS .32. REACTIVITY STUDIES OF THE PENDANT CARBOXYLIC GROUP IN A MACROCYCLIC CU-2+ COMPLEX TOWARDS AMIDE FORMATION AND ITS USE AS A PROTEIN-LABELING AGENT

The Cu2+ complex of 1, having a non‐coordinating carboxylic group, can be reacted under the typical conditions of peptide formation with amines such as 2‐methylpropylamine or (pyrid‐2‐yl)methylamine to give, after removal of Cu2+ with CN−, the amides 4 and 5. The Cu2+ ion is of paramount importance since it protects the four amino groups of the macrocycle so that the amide condensation can specifically be done with the exogenous amine It is also shown that the Cu2+ complex of 1 can be covalently attached to bovine serum albumin (BSA), thus opening the possibility to use this compound as a labelling agent for proteins and antibodies. Copyright © 1990 Verlag GmbH & Co. KGaA, Weinheim