Intramolecular hydrogen bonding allows simple enaminones to structurally mimic the i, i + 4, and i + 7 residues of an α-helix

Johanna M. Rodriguez, Andrew D. Hamilton

Research output: Contribution to journalArticlepeer-review

Abstract

An intramolecularly hydrogen bonded enaminone scaffold was designed and synthesized in order to mimic the i, i + 4, and i + 7 residues of an α-helix. The resonance stabilized vinylogous amide group serves as an aromatic ring isostere and allows the positioning and angular projection of the R-groups in a manner similar to an α-helix.

Original languageEnglish (US)
Pages (from-to)7443-7446
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number42
DOIs
StatePublished - Oct 16 2006

Keywords

  • Enaminone
  • Hydrogen bonding
  • α-Helix mimetic

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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