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Impact of substituent effects on the design of β-sheet mimetics and β-double helices from (E)-vinylogous γ-amino acid oligomers

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Abstract

Here we report the design, single crystal conformations, impact of the substituents and structural differences of two structurally important motifs, β-sheets and β-double helices. Though β-sheets are common structural motifs in protein structures, β-double helices are not common in proteins and peptides. We found that both β-sheet mimetics and β-double helices can be constructed from the homooligomers of α,β-unsaturated γ-amino acids. Results suggested that introducing gem-dialkyl substitutions at the γ-carbon of the homooligomer of α,β-unsaturated γ-amino acids resulted in the β-double helix conformation, while the same oligomer with monosubstitution at the γ-carbon displayed a β-sheet structure.

Graphical abstract: Impact of substituent effects on the design of β-sheet mimetics and β-double helices from (E)-vinylogous γ-amino acid oligomers

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Publication details

The article was received on 15 Aug 2019, accepted on 27 Sep 2019 and first published on 27 Sep 2019


Article type: Paper
DOI: 10.1039/C9OB01801H
Org. Biomol. Chem., 2019, Advance Article

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    Impact of substituent effects on the design of β-sheet mimetics and β-double helices from (E)-vinylogous γ-amino acid oligomers

    K. Veeresh, M. Singh and H. N. Gopi, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01801H

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