Functionalized oligoanthranilamides: Modular and conformationally controlled scaffolds

Yoshitomo Hamuro, Andrew D. Hamilton

Research output: Contribution to journalArticlepeer-review


This paper describes the use of functionalize oligoanthranilamides as conformationally controlle scaffolds for molecular recognition. Oligomers of anthranilamides are stabilize by the formation of intramolecular six-membere hydrogen bonds in a linear strand conformation. Onto alternate anthranilic aci units, we have attached di- or tripeptide recognition units with the potential to form intramolecular hydrogen bonds to an intercalated peptide strand . Using 1H NMR dilution experiments in CDCl3, we have observe chemical shift changes that are consistent with the formation of an extended hydrogen bondes sheet dimer. We also demonstrate that the bis-alanine functionalize strands are able to form discrete hydrogen bonded complexes with dipeptide substrates an to bind hexanoyl alanylalanine selectively over its benzyl ester. In the presence of excess hydrogen bon donors and acceptors, the oligoanthranilamide strand retained its linear conformation, pointing to the potential of this modular design as a useful and stable scaffold for molecular recognition studies.

Original languageEnglish (US)
Pages (from-to)2355-2363
Number of pages9
JournalBioorganic and Medicinal Chemistry
Issue number9
StatePublished - 2001

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


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