Flat, C-alpha,C-beta-Didehydroalanine Foldamers with Ferrocene Pendants: Assessing the Role of alpha-Peptide Dipolar Moments
The foldamer field is continuously expanding as it allows to produce molecules endowed with 3D-structures and functions never observed in nature. We synthesized flat foldamers based on the natural, but non-coded, C-alpha,C-beta-didehydroalanine alpha-amino acid, and covalently linked to them two fer...
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| Veröffentlicht in: | ChemPlusChem (Weinheim, Germany) Germany), 2021-05, Vol.86 (5), p.723-730 |
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| container_title | ChemPlusChem (Weinheim, Germany) |
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| creator | Santi, Saverio Bisello, Annalisa Cardena, Roberta Tomelleri, Silvia Schiesari, Renato Biondi, Barbara Crisma, Marco Formaggio, Fernando |
| description | The foldamer field is continuously expanding as it allows to produce molecules endowed with 3D-structures and functions never observed in nature. We synthesized flat foldamers based on the natural, but non-coded, C-alpha,C-beta-didehydroalanine alpha-amino acid, and covalently linked to them two ferrocene (Fc) moieties, as redox probes. These conjugates retain the flat and extended conformation of the 2.0(5)-helix, both in solution and in the crystal state (X-ray diffraction). Cyclic voltammetry measurements agree with the adoption of the 2.0(5)-helix, characterized by a negligible dipole moment. Thus, elongated alpha-peptide stretches of this type are insulators rather than charge conductors, the latter being constituted by peptide alpha-helices. Also, our homo-tetrapeptide has a N-to-C length of about 18.2 angstrom, almost double than that (9.7 angstrom) of an alpha-helical alpha-tetrapeptide. |
| doi_str_mv | 10.1002/cplu.202100072 |
| format | Article |
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| subjects | Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology |
| title | Flat, C-alpha,C-beta-Didehydroalanine Foldamers with Ferrocene Pendants: Assessing the Role of alpha-Peptide Dipolar Moments |
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