Synthesis and conformational studies of short mixed γ/α-glycopeptides based on sugar γ 3,3 -amino acids

Mylène Richard (1) , Anne-Sophie Felten (1) , Francoise Chrétien (1) , Marie-Christine Averlant-Petit (2) , Nadia Pellegrini-Moise (1)

1 SRSMC - Structure et Réactivité des Systèmes Moléculaires Complexes
2 LCPM - Laboratoire de Chimie Physique Macromoléculaire

Carbohydrates bearing both amino and carboxylate groups could be useful for expanding the repertoire of monomers used for building foldamers. In this paper, we give a full account of the synthesis of small hybrid g/a-glycopeptides built with sugar g-amino acids and L-alanine. The g/a-glycopeptides obtained are the first featuring geminally b,b-disubstituted g-amino acids in which the b-carbon is the pseudo anomeric carbon of a sugar ring. Their conformational properties were studied by NMR and solution infrared spectroscopy, circular dichroism and molecular dynamics simulation.

Mots clés: Carbohydrates; Sugar amino acids; Glycopeptides; Foldamers

Domaines: Chimie

Mylène Richard, Anne-Sophie Felten, Francoise Chrétien, Marie-Christine Averlant-Petit, Nadia Pellegrini-Moise. Synthesis and conformational studies of short mixed γ/α-glycopeptides based on sugar γ 3,3 -amino acids. Tetrahedron, 2017, 73 (48), pp.6795 - 6804. ⟨10.1016/j.tet.2017.10.038⟩. ⟨hal-01629811⟩