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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N-substituted Glycines
Peptoids
Peptidomimetics
Alkynes
Azides
Cycloaddition
Fluorophores
Cycloaddition Reaction
Oligomers
Scaffolds
Display devices
Peptides
cycloaddition
alkynes
Substrates
glycine
conjugation
oligomers
peptides
solid phases

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Click to fit : Versatile polyvalent display on a peptidomimetic scaffold. / Jang, Hangjun; Fafarman, Aaron; Holub, Justin M.; Kirshenbaum, Kent.

In: Organic Letters, Vol. 7, No. 10, 12.05.2005, p. 1951-1954.

Research output: Contribution to journalArticle

Jang, Hangjun ; Fafarman, Aaron ; Holub, Justin M. ; Kirshenbaum, Kent. / Click to fit : Versatile polyvalent display on a peptidomimetic scaffold. In: Organic Letters. 2005 ; Vol. 7, No. 10. pp. 1951-1954.
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