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Updated: Dec 27, 2025

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Design and Synthesis of Backbone-Fused, Conformationally Constrained Morpholine-Proline Chimeras
Sofiane Hocine1, Gilles Berger2, Stephen Hanessian1
1Department of Chemistry, Université de Montréal, Station Centre-Ville, C.P. 6128, Montreal, Quebec H3C 3J7, Canada.
Abstract:
We 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.
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