Facile synthesis of benzamides to mimic an α-helix

Jung Mo Ahn, Sun Young Han

Research output: Contribution to journalArticle

55 Scopus citations

Abstract

A new α-helix mimetic was designed by using a benzamide as a rigid scaffold. It presents three functional groups corresponding to side chains of amino acids found at the i, i + 4, and i + 7 positions of an ideal α-helix, which are displayed on the same helical face. Its efficient synthesis was achieved by employing simple alkylation and amidation reactions which can be easily adapted for solid-phase synthesis. As a result, two tris-benzamides were produced to mimic two helical regions found in a peptide hormone, glucagon.

Original languageEnglish (US)
Pages (from-to)3543-3547
Number of pages5
JournalTetrahedron Letters
Volume48
Issue number20
DOIs
StatePublished - May 14 2007

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Keywords

  • Benzamide scaffold
  • Glucagon antagonists
  • Inhibitors for protein-protein interaction
  • α-Helix mimetics

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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