Synthesis, Conformation, and Interactions with Small Molecules of Bis(Cyclic Dipeptides)

Article abstract of DOI:10.1002/hlca.19820650315

Bis(cyclic dipeptides), cyclo<*>(Lys-Pro)cyclo(Glu-Pro) and S,S'-bis(cyclo)hemiCys-Pro), were synthesized.These bis(cyclic dipeptides) very efficiently formed complexes with Ba²⁺ and Na⁺ owing to intramolecular cooperation of two cyclic dipeptide moieties, the bis effect.Cyclo<*>(Lys-Pro)cyclo(Glu-Pro) stacked sodium 8-anilino-1-napthalensulfonate in aqueous solution.These properties of complexation were controlled by the nature of the bridge connecting two cyclic dipeptide moieties.The geometry of the complex between S,S'-bis(cyclo(hemiCys-Pro)) and metal ion was investigated with the help of circular dichroism, nuclear magnetic resonance, and Raman spectroscopy.