Click to fit: Versatile polyvalent display on a peptidomimetic scaffold

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

doi:10.1021/ol050371q

Click to fit: Versatile polyvalent display on a peptidomimetic scaffold

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

Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	1951-1954
Number of pages	4
Journal	Organic Letters
Volume	7
Issue number	10
DOIs	https://doi.org/10.1021/ol050371q
State	Published - May 12 2005

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol050371q

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AU - Holub, Justin M.

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AB - (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.

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Click to fit: Versatile polyvalent display on a peptidomimetic scaffold

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