engleski

The influence of different ferrocene scaffolds on conformational properties of derived peptidomimetics

The organometallic conjugates derived from 1, n- disubstituted ferrocenes and Ala were extensively studied for their ability to adopt the turn or - sheet-like structures. It was shown that hydrogen- bond donor/acceptor 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 [2], while conjugation with diamino-functionalized ferrocene lead to the 14-membered hydrogen- bonded rings. Herein, we report the synthesis of the conjugates I, II and III composed of three different types of turn-nucleating ferrocene scaffolds and Leu, Val or Phe, respectively. The influence of the structurally diverse ferrocene scaffolds and the bulkiness of amino acid side chains on the conformational properties of the derived bioconjugates is explored by IR, NMR and CD spectroscopy.

ferrocene diamine ; peptidomimetics: bioconjugates

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