Induced circular-dichroism chirality probes for selective amino acid detection through screening of a dynamic combinatorial library of lanthanide complexes

Abstract

A dynamic combinatorial library of lanthanide complexes was prepared to develop induced-circular-dichroism (CD) chirality probes. It totaled 168 combinations of coordinative N-aromatic chromophores, trivalent lanthanide centers, and guest amino acids. Eu(3+) and Tb(3+) complexes prepared with quinolinecarboxylic acid were particularly effective as induced-CD chirality probes for selective alanine detection, whereas a Yb(3+) complex with terpyridine exhibited glutamine selectivity. The former two complexes highly preferred alanine to the corresponding amine, ester, amino alcohol, and carboxylic acid derivatives. As such, the present combinatorial screening of a dynamic lanthanide complex library has led to a new series of induced-CD chirality probes for specific amino acids.