Fit to be tied: Conformation-directed macrocyclization of peptoid foldamers

Justin M. Holub, Hangjun Jang, Kent Kirshenbaum

Research output: Contribution to journalArticle

Abstract

Covalent macrocyclic constraints can be readily installed on N-substituted glycine "peptoid" oligomer substrates. Cu(I)-catalyzed [3+2] cycloaddition reactions were conducted on solid support to ligate peptoid side chain azide and alkyne functionalities. Intramolecular macrocycle formation is facilitated by preorganizing the reactive groups across one turn of the helical secondary structure. These results confirm that conformational ordering can be exploited to assist the macrocyclization of folded oligomers.

Original languageEnglish (US)
Pages (from-to)3275-3278
Number of pages4
JournalOrganic Letters
Volume9
Issue number17
DOIs
StatePublished - Aug 16 2007

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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