engleski

Structural Analysis of Oligopeptides Containing Ferrocene Amino Acids as Potential Beta-turn Mimics

In continuation of our studies in the field of heteroannularly substituted ferrocene amino acids 1 (m, n = 0-3) and their derivatives, we reported about coupling of their N-Boc derivatives with L-alanine into oligopeptides 2 (m, n = 0-3 ; p, r = 1-2) using EDC/ HOBt protoco. A number of a ferrocene-containing oligopeptides with parallel substituting strands (NHCHRCO)n were prepared starting from 1, 1'-Fn(COOH)2 and studied as a beta-sheet models. It is worth mentioning that compounds 2 are the first example of ferrocene-containing oligomers with antiparallel strands. These conjugates containing 1, 1'-ferrocenylene unit as beta-turn inducer are expected to be better mimics of ordinary natural beta-sheets than the parallel ones. In the present work we have carried out a detailed structural study on possible interstrand contacts in oligopeptides 2. For this purposes we have analysed their IR and NMR spectra in solvents which themselves do not form hydrogen bonds.

ferrocene-containing oligopeptides; beta-turn mimics; structural analysis

nije evidentirano