jo9b03413_si_001.pdf (4.21 MB)
Design and Synthesis of Backbone-Fused, Conformationally Constrained Morpholine-Proline Chimeras
journal contribution
posted on 2020-03-05, 13:05 authored by Sofiane Hocine, Gilles Berger, Stephen HanessianWe report the synthesis
of two novel bridged morpholine-proline
chimeras 4 and 5, which represent rigid
conformationally locked three-dimensional structures wherein the lone
pairs of electrons on oxygen and nitrogen are oriented in spatially
different “east–west” and “north–west”
directions, respectively. In combination with the presence of a carboxylic
acid, the electronic features of these compounds may be useful in
the context of peptidomimetic design of biologically relevant compounds.
Quantitative estimates of the basicity of the nitrogen atoms were
obtained using conceptual density functional theory analysis.