beta-Pseudopeptide foldamers. The homo-oligomers of (4R)-(2-oxo-1,3-oxazolidin-4-yl)-acetic acid (D-Oxac).
A total synthesis in solution and a conformational analysis of the homo-oligomers of (4R)-(2-oxo-1,3-oxazolidin-4-yl)-acetic acid (D-Oxac) to the tetramer level are described. As the D-Oxac building block contains both an oxazolidin-2-one and a beta-amino acid group, it may represent a new type of conformationally constrained tool for the construction of beta-pseudopeptide foldamers. A conformational investigation using NMR and an extensive, unconstrained analysis with a Monte Carlo search to the octamer level, both in water and in chloroform, showed that these homo-oligomers tend to fold in a regular helical structure in a competitive solvent, such as water. Since aqueous solutions are of major relevance for biological systems, these molecules are good candidates for application to these environments.
Department of Chemistry "G. Ciamician", Alma Mater Studiorum, University of Bologna, 40126 Bologna, Italy.
Gianluigi
G
Luppi
Roberta
R
Galeazzi
Marco
M
Garavelli
Fernando
F
Formaggio
Claudia
C
Tomasini
D000596:Amino Acids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009010:Monte Carlo Method; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000494:pharmacology; D010080:Oxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D023303:Oxazolidinones / Q000737:chemistry*; D017433:Protein Structure, Secondary; D012997:Solvents / Q000737:chemistry
C503044:(2-oxo-1,3-oxazolidin-4-yl)-acetic acid; D000596:Amino Acids; D009842:Oligopeptides; D010080:Oxazoles; D023303:Oxazolidinones; D012997:Solvents