Click to fit: Versatile polyvalent display on a peptidomimetic scaffold

Hangjun Jang, Aaron Fafarman, Justin M. Holub, Kent Kirshenbaum

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) We describe an efficient protocol to effect multisite conjugation reactions to oligomers on solid-phase support. Sequence-specific N-substituted glycine "oligopeptoids" were utilized as substrates for azide-alkyne cycloaddition reactions. Diverse groups, including nucleobases and fluorophores, were conjugated at up to six positions on peptoid side chains with yields ranging from 88 to 96%. This strategy will be broadly applicable for generating polyvalent displays on peptides and other scaffolds, allowing precise control of spacing between the displayed groups.

Original languageEnglish (US)
Pages (from-to)1951-1954
Number of pages4
JournalOrganic Letters
Volume7
Issue number10
DOIs
StatePublished - May 12 2005

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ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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