Flack, TheoTheoFlackRomain, CharlesCharlesRomainWhite, AndrewAndrewWhiteHaycock, PeterPeterHaycockBarnard, AnnaAnnaBarnard2019-07-222019-07-222019-06-21Organic Letters, 2019, 21 (12), pp.4433-44381523-7052http://hdl.handle.net/10044/1/71702The 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.© 2019 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.Science & TechnologyPhysical SciencesChemistry, OrganicChemistryPROTEIN-PROTEIN INTERACTIONSEXPLORING KEY ORIENTATIONSSMALL-MOLECULE INHIBITORSROTATIONINTERFACESAMIDE03 Chemical SciencesOrganic ChemistryJournal Articlehttps://www.dx.doi.org/10.1021/acs.orglett.9b01115https://pubs.acs.org/doi/10.1021/acs.orglett.9b01115105603/Z/14/Z