engleski

Syynthesis and conformational analysis of peptidomimetics composed of ferrocene-1, 1'- diamine and natural amino acids

1, n-Disubstituted ferrocenes were established as molecular templates for the design of turns and β- 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 with natural amino acids or peptides. It was clearly demonstrated that hydrogen bond donating/accepting properties of turn-inducing ferrocene scaffolds regulate the hydrogen bonding patterning of the derived peptides: the 10-membered interstrand hydrogen- bonded rings were established in the conjugates of the amino acids or peptides with dicarbonyl- functionalized ferrocene core, the 12-membered rings were formed in their conjugates with -NH-Fn- CO- moiety, while conjugation with diamino- functionalized ferrocene lead to the 14-membered hydrogen-bonded rings (also labelled as two simultaneous 10-membered β-turns) in the corresponding symmetrically disubstituted conjugates. Herein, we report the synthesis of orthogonally protected and desymmetrized peptides 1 and 2 composed of turn-nucleating ferrocene-1, 1’-diamine unit and homo- or heterochiral amino acid sequences. The effects of the backbone chirality and N-terminal protecting group on the conformational properties of the novel peptidomimetics are explored by IR, NMR and CD spectroscopy. The spectroscopic studies were augmented with DFT calculations.

Ferrocene ; Peptidomimetic ; Conformational Analysis

nije evidentirano