Oxazolopiperidin-2-ones as type II' beta-turn mimetics: synthesis and conformational analysis.
We describe a straightforward synthesis of 9-substituted 3-aminooxazolidinopiperidin-2-ones 4. Some derivatives were prepared for use in peptide synthesis as rigidified surrogates of the Ala-Pro dipeptide. Analysis of the amide derivatives 14 by NMR experiments and molecular mechanics/dynamics calculations shows that the major isomer 14a has a stronger propensity than the minor isomer 14b to adopt beta-turn conformations, and the calculations indicate that in water 14a adopts a stable betaII' turn conformation.
Estiarte
M A
MA
Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, c/Martí i Franquès, 08028-Barcelona, Spain.
Rubiralta
M
M
Diez
A
A
Thormann
M
M
Giralt
E
E
D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D018716:Molecular Mimicry; D010455:Peptides / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D017433:Protein Structure, Secondary; D013237:Stereoisomerism
D010455:Peptides; D010880:Piperidines