Phe-Ala-based diazaspirocyclic lactam as nucleator of type II' β-turn.


The synthesis of a novel Phe-Ala dipeptide mimic, built up on a diazaspirocyclic lactam core, is presented. This new scaffold was evaluated for conformational mimicry of reverse turn by combining molecular modeling, IR, NMR, and X-ray diffraction experiments. All these tools agree on the presence of a strong intramolecular hydrogen bond, thus demonstrating the ability of this spiro compound to act as a type II' β-turn inducer.

DOI: 10.1021/jo1019927

Cite this paper

@article{Sacchetti2011PheAlabasedDL, title={Phe-Ala-based diazaspirocyclic lactam as nucleator of type II' β-turn.}, author={Alessandro Sacchetti and Alessandra Silvani and Giordano Lesma and Tullio Pilati}, journal={The Journal of organic chemistry}, year={2011}, volume={76 3}, pages={833-9} }