Impact of substituent effects on the design of β-sheet mimetics and β-double helices from (E)-vinylogous γ-amino acid oligomers. Issue 41 (9th October 2019)

• Record Type: Journal Article
• Authors: Veeresh, Kuruva; Singh, Manjeet; Gopi, Hosahudya N.
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 41(2019)
• Page Start: 9226
• Page End: 9231
• Publication Date: 2019-10-09
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob01801h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The impact of substituent effects at the γ-carbon on the structures of ( E )-vinylogous γ-amino acid homooligomers is studied. 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.