engleski

Peptidomimetics derived from ferrocene mono- and diamines

Ferrocene-peptide conjugates present useful and efficient bioorganometallic constraint designed to induce chirally organized structures through intramolecular hydrogen bonding as a prerequisite for 3D structure formation and function of biological systems. As opposed to well-documented peptides derived from ferrocene-1, 1’-dicarboxylic acid (Fcda) and 1’-aminoferrocene-1-carboxylic acid (Fca) [1], only two representatives of peptides I derived from ferrocene-1, 1’-diamine were reported [2]. We have established a facile and efficient synthetic route for preparation of peptides I which does not include unstable Fcda synthon. Recently, we have showed that introduction of minimum-sized peptide chain on aminoferrocene II led to the formation of a β-turn-like structure originating from intrachain hydrogen- bonding. Herein, we present the synthesis of peptides I and II bearing homo- and heterochiral Ala-Pro sequences followed by extensive studies of their conformational preferences in solution as well as in solid state.

Ferrocene ; Proline ; Peptidomimetic ; Intramolecular hydrogen bond ; Conformational analysis

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