The two epimers Boc-L-Phe-D-Oxd-(S)-β3-hPhg-OBn (1) and Boc-L-Phe-D-Oxd-(R)-β3-hPhg-OBn (2) have been prepared by standard methods in solution, and their conformation was analyzed both in solution and in the solid state. While in solution 1 shows a random coil structure, 2 tends to assume a γ-turn conformation that is nearly retained in the solid state. On the other hand, in the solid state molecules of 1 associate generating a helix that involves the formation of elongated crystals with hexagonal cross-section. This effect is not observed in the crystals formed by Boc-L-Phe-D-Oxd-(R)-β3-hPhg-OBn 2. © 2009 American Chemical Society.
Pseudopeptides designed to form supramolecular helixes: The role of the stereogenic centers
Angelici, Gaetano;Tomasini, Claudia
2010-01-01
Abstract
The two epimers Boc-L-Phe-D-Oxd-(S)-β3-hPhg-OBn (1) and Boc-L-Phe-D-Oxd-(R)-β3-hPhg-OBn (2) have been prepared by standard methods in solution, and their conformation was analyzed both in solution and in the solid state. While in solution 1 shows a random coil structure, 2 tends to assume a γ-turn conformation that is nearly retained in the solid state. On the other hand, in the solid state molecules of 1 associate generating a helix that involves the formation of elongated crystals with hexagonal cross-section. This effect is not observed in the crystals formed by Boc-L-Phe-D-Oxd-(R)-β3-hPhg-OBn 2. © 2009 American Chemical Society.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
