Clickity-click: Highly functionalized peptoid oligomers generated by sequential conjugation reactions on solid-phase support

Justin M. Holub, Hangjun Jang, Kent Kirshenbaum

Research output: Contribution to journalArticle

Abstract

N-Substituted glycine peptoid oligomers were used as substrates for azide-alkyne [3 + 2] cycloaddition conjugation reactions and then elaborated through additional rounds of oligomerization and cycloaddition. This novel sequential conjugation technique allowed for the generation of complex peptidomimetic products in which multiple heterogeneous pendant groups were site-specifically positioned along the oligomer scaffold. Studies of a water-soluble estradiol-ferrocene peptoid conjugate demonstrated a potential application for the modular synthesis of biosensors.

Original languageEnglish (US)
Pages (from-to)1497-1502
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume4
Issue number8
DOIs
StatePublished - 2006

Fingerprint

Peptoids
Cycloaddition
Cycloaddition Reaction
cycloaddition
conjugation
oligomers
Oligomers
N-substituted Glycines
solid phases
Peptidomimetics
Oligomerization
Alkynes
Azides
Biosensing Techniques
alkynes
glycine
bioinstrumentation
Biosensors
Scaffolds
Estradiol

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry(all)

Cite this

Clickity-click : Highly functionalized peptoid oligomers generated by sequential conjugation reactions on solid-phase support. / Holub, Justin M.; Jang, Hangjun; Kirshenbaum, Kent.

In: Organic and Biomolecular Chemistry, Vol. 4, No. 8, 2006, p. 1497-1502.

Research output: Contribution to journalArticle

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