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All-thioamidated homo-alpha-peptides: synthesis and conformation (Articolo in rivista)

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All-thioamidated homo-alpha-peptides: synthesis and conformation (Articolo in rivista) (literal)

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F. Formaggio, M. Crisma, C. Toniolo, C. Peggion (2013)
All-thioamidated homo-alpha-peptides: synthesis and conformation
in European journal of organic chemistry (Print)
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Institute of Biomolecular Chemistry, Padova Unit, CNR, Department of Chemistry, University of Padova, 35131 Padova, Italy (literal)

Titolo

Abstract

Replacement of a peptide bond with its thioamide surrogate is a classical method for the generation of a peptidomimetic with altered spectroscopic, conformational, physicochemical, and biological properties. In this context, we synthesized short series of terminally protected homo-alpha-oligopeptides based on the alpha-amino acids Gly, Ala, and Nle, as well as their corresponding fully thioamidated analogues. For the first time, the preparation of the latter compounds was achieved in single-step fashion through direct thionation of their oxygenated precursors. Using X-ray diffraction analysis and NMR spectroscopy we were also able to confirm that the thioamidated alpha-amino acid residues can easily adopt either folded or fully extended conformations. (literal)

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