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Synthesis and conformational study of monosubstituted aminoferrocene-based peptides bearing homo- and heterochiral pro-ala sequences

The synthesis and conformational analysis of a series of the monosubstituted aminoferrocene-based peptides bearing homo- and heterochiral Pro-Ala sequences are described. A change of the Pro amino acid chirality can affect the secondary structure. A homochiral derivatives of t-BuCO-AA2-AA1-NHFc favour β-turns, and a disruption of the secondary structure is observed in their heterochiral analogues in solution. A detailed computational study suggested formation of γ-turns in their heterochiral derivatives. The X-ray determined crystal structures of heterochiral compounds show preference for β-turns. The calculated interaction energies pointed out the significance of the intermolecular hydrogen bonds favourable enough to overcome rearangement of a single molecule from the most stable conformer to the one adopted in the solid state. The current research pointed out the potential of the investigated compounds for the fine tuning of their conformational properties by variation of the chirality of constituted amino acids.

conformational analysis ; DFT (Density Functional Theory) ; ferrocene peptides ; hydrogen bonding ; NMR

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