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.
Luppi
Gianluigi
G
Department of Chemistry "G. Ciamician", Alma Mater Studiorum, University of Bologna, 40126 Bologna, Italy.
Galeazzi
Roberta
R
Garavelli
Marco
M
Formaggio
Fernando
F
Tomasini
Claudia
C
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