Moretto Alessandro, Peggion Cristina, Formaggio Fernando, Crisma Marco, Kaptein Bernard, Broxterman Quirinus B, Toniolo Claudio
Institute of Biomolecular Chemistry, CNR, Department of Chemistry, University of Padova, Padova, Italy.
Chirality. 2005 Oct;17(8):481-7. doi: 10.1002/chir.20182.
Reactions of a racemic amine with chiral, N(alpha)-acetylated, C(alpha)-methyl l-phenylglycine-based dipeptide 5(4H)-oxazolones proceed diastereoselectively to give predominantly dipeptide alkylamides comprising d-alpha-phenylethylamine. Diastereoselectivity is remarkably sensitive to solvent polarity and reaction temperature but not significantly to the nature of the C(alpha)-tetrasubstituted alpha-amino acid at position 1 of the dipeptide. The beta-turn 3D structures of the aminolysis products were established in CDCl(3) solution by FT-IR absorption and in one case in the crystal state by X-ray diffraction as well.
