307990-71-2Relevant academic research and scientific papers
Oxazolopiperidin-2-ones as type II' β-turn mimetics: Synthesis and conformational analysis
Estiarte,Rubiralta,Diez,Thormann,Giralt
, p. 6992 - 6999 (2000)
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 β-turn conformations, and the calculations indicate that in water 14a adopts a stable βII' turn conformation.
