All-Thioamidated Homo--Peptides: Synthesis and Conformation

作者：Formaggio Fernando^*; Crisma Marco; Toniolo Claudio; Peggion Cristina

来源：European Journal of Organic Chemistry, 2013, 2013(17): 3455-3463.

DOI：10.1002/ejoc.201300050

• Conformation analysis
• Synthetic methods
• Peptides
• Peptidomimetics

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--oligopeptides based on the -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 -amino acid residues can easily adopt either folded or fully extended conformations.

• 出版日期2013-6