engleski

SYNTHESIS AND CONFORMATIONAL ANALYSIS OF FERROCENE PEPTIDOMIMETICS

Reverse turns are involved in protein folding and molecular recognition processes mediated through interactions of side chains within the turns with various receptor domains. The beta-turns, an essential components of beta-sheets, are considered as a nucleators that bring the two peptide strands in close proximity, enabling their interactions through hydrogen bonding. 1, n-Disubstituted ferrocenes are recognized as molecular templates for the design of turns and -sheet-like structures as the almost free rotating cyclopentadiene rings are separated by about 3.3 Å which is ideal for interstrand hydrogen bonding in their conjugates comprised of natural amino acids or peptides. Taking into account the peptide groups directly attached to the ferrocene core, the three major classes of bioconjugates I-III, derived from ferrocene-1, 1’-dicarboxylic acid [(Fcd), I], [1] 1’-amino-ferrocene-1-carboxylic acid [(Fca), II][2] and ferrocene-1, 1’-diamine [(Fcda), III], [3] need to be considered. The ferrocene scaffolds Fcd, Fca and Fcda were recognized as a turn inducers in peptides I-III owing to the presence of 10- (I), 12- (II) and 14-membered (III) intramolecularly hydrogen bonded (IHB) rings. A detailed conformational analysis based on spectroscopic (IR, NMR, CD) and computational study together with X-ray crystal structure analysis was performed to determine IHB patterns of bioconjugates I-III and to discuss (di)similarities in solution and in the solid state.

Ferrocene; Peptidomimetic; Conformational Analysis

nije evidentirano