Alkyne-linked 2,2-disubstituted-indolin-3-one oligomers as extended β-strand mimetics

Pauline N. Wyrembak, Andrew D. Hamilton

Research output: Contribution to journalArticlepeer-review

Abstract

The design, synthesis, and structural analysis of a new foldamer that mimics an extended β-sheet are presented. The nonpeptidic mimetic is based on a series of 2,2-disubstitutedindolin-3-one groups linked through their 4,7-positions by an alkyne spacer. An intramolecular hydrogen bond between the carbonyl of one indolinone subunit and the proximal NH of another subunit imposes a conformation that mimics the side chain positioning on a β-strand. X-ray crystallographic studies support the presence of this intramolecular hydrogen bond. The described approach allows extension of the scaffold to longer oligomers that will form the basis of new mimetics for the disruption of therapeutically relevant protein-protein interactions that rely on the contacts of side chain residues on two β-strands.

Original languageEnglish (US)
Pages (from-to)4566-4567
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number13
DOIs
StatePublished - Apr 8 2009

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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