Inhaltszusammenfassung

Formal CH2 insertion in bioconjugates composed of 1'-aminoferrocene-1-carboxylic acid (Fca) and alanine Boc-Ala-Fca-Ala-OCH3 gives Fca bioconjugates with the beta-amino acid (S)-3-amino-2-methylpropanoic acid (Aib). The novel homologous conjugates of ferrocene were fully characterized by spectroscopic and analytical methods. NMR, CD and IR spectroscopy in concert with DFT calculations suggest that the formal "L-Ala-to-(S)-beta-Aib mutations" can exert ferrocene helix inversion due to t...Formal CH2 insertion in bioconjugates composed of 1'-aminoferrocene-1-carboxylic acid (Fca) and alanine Boc-Ala-Fca-Ala-OCH3 gives Fca bioconjugates with the beta-amino acid (S)-3-amino-2-methylpropanoic acid (Aib). The novel homologous conjugates of ferrocene were fully characterized by spectroscopic and analytical methods. NMR, CD and IR spectroscopy in concert with DFT calculations suggest that the formal "L-Ala-to-(S)-beta-Aib mutations" can exert ferrocene helix inversion due to the different stereogenic carbon atoms of L-Ala and (S)-beta-Aib. Furthermore, the mutation (de-)stabilizes the conserved secondary structure with two intramolecular hydrogen bonds, depending on the "mutation site". The systematic work presented provides a firm basis for understanding the factors that determine folding in bioconjugates of ferrocene and beta-amino acids and will guide the rational design of metallocene peptidomimetics incorporating beta-amino acids. » weiterlesen» einklappen

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DDC Sachgruppe:
Chemie