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 Hamilton

Research output: Contribution to journalArticle

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

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Hydrogen Bonding
Scaffolds
Amides
Hydrogen
Hydrogen bonds

Keywords

  • α-Helix mimetic
  • Enaminone
  • Hydrogen bonding

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Intramolecular hydrogen bonding allows simple enaminones to structurally mimic the i, i + 4, and i + 7 residues of an α-helix. / Rodriguez, Johanna M.; Hamilton, Andrew.

In: Tetrahedron Letters, Vol. 47, No. 42, 16.10.2006, p. 7443-7446.

Research output: Contribution to journalArticle

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