N-{N-[2-(3,5-Difluorophenyl)acetyl]-(S)-alanyl}-(S)-phenylglycine tert-butyl ester (DAPT): an inhibitor of γ-secretase, revealing fine electronic and hydrogen-bonding features.

ABSTRACT: The title compound, C(23)H(26)F(2)N(2)O(4), is a dipeptidic inhibitor of γ-secretase, one of the enzymes involved in Alzheimer's disease. The molecule adopts a compact conformation, without intramolecular hydrogen bonds. In the crystal structure, one of the amide N atoms forms the only intermolecular N-H...O hydrogen bond; the second amide N atom does not form hydrogen bonds. High-resolution synchrotron diffraction data permitted the unequivocal location and refinement without restraints of all H atoms, and the identification of the characteristic shift of the amide H atom engaged in the hydrogen bond from its ideal position, resulting in a more linear hydrogen bond. Significant residual densities for bonding electrons were revealed after the usual SHELXL refinement, and modeling of these

SUBMITTER: Czerwinski A 

PROVIDER: S-EPMC3014104 | biostudies-literature | 2010 Dec

REPOSITORIES: biostudies-literature