Catalytic hydrogenation of vinylogous peptides: a route towards γ-peptide foldamers |
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| Authors: | Claude Grison,Sté phane Genè veSté phanie Claudel,Philippe CoutrotMichel Marraud |
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| Affiliation: | a Laboratoire de Chimie Organique Biomoléculaire, Institut Nancéien de Chimie Moléculaire, FR CNRS 1742, UMR 7565, Université Henri Poincaré, Nancy 1, BP 239, 54506 Vandoeuvre cédex, France
b Laboratoire de Chimie Physique Macromoléculaire, UMR 7568, ENSIC-INPL, BP 451, 54001 Nancy, France |
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| Abstract: | Catalytic hydrogenation over Pd/C of vinylogous aminoacids and aminoamides has been studied. The configuration of the ethylenic bond has an important effect on the diastereoselectivity. The higher selectivity is observed with the E-vinylogous aminoamides. The conformational preferences of the α,γ-disubstituted γ-peptides have been determined. The 2S,4S-γ-peptide moiety induces a β-like folded structure stabilized by an intramolecular hydrogen bond, whereas the 2S,4R-diastereomer assumes an open structure. |
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