Journal
ORGANIC LETTERS
Volume 21, Issue 12, Pages 4433-4438Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01115
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Funding
- Imperial College London
- Wellcome Trust [105603/Z/14/Z]
- Wellcome Trust [105603/Z/14/Z] Funding Source: Wellcome Trust
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The design, synthesis, and conformational analysis of an oligobenzanilide helix mimetic scaffold capable of simultaneous mimicry of two faces of an alpha-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 alpha-helix.
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