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Design, Synthesis, and Conformational Analysis of Oligobenzanilides as Multifacial α-Helix Mimetics

Author:
Flack, Theo, Romain, Charles, White, Andrew J. P., Haycock, Peter R., Barnard, Anna
Source:
Organic letters 2019 v.21 no.12 pp. 4433-4438
ISSN:
1523-7052
Subject:
chemical reactions, models, molecular conformation, organic compounds, plasticity
Abstract:
The design, synthesis, and conformational analysis of an oligobenzanilide helix mimetic scaffold capable of simultaneous mimicry of two faces of an α-helix is reported. The synthetic methodology provides access to diverse monomer building blocks amenable to solid-phase assembly in just four synthetic steps. The conformational flexibility of model dimers was investigated using a combination of solid and solution state methodologies supplemented with DFT calculations. The lack of noncovalent constraints allows for significant conformational plasticity in the scaffold, thus permitting it to successfully mimic residues i, i+2, i+4, i+6, i+7, and i+9 of a canonical α-helix.
Agid:
6478146