Rapid multistep synthesis of a bioactive peptidomimetic oligomer for the undergraduate laboratory

Yeliz Utku, Abhinav Rohatgi, Barney Yoo, Kent Kirshenbaum, Ronald N. Zuckermann, Nicola L. Pohl

Research output: Contribution to journalArticle

Abstract

Peptidomimetic compounds are increasingly important in drug-discovery applications. We introduce the synthesis of an N-substituted glycine oligomer, a bioactive "peptoid" trimer. The six-step protocol is conducted on solid-phase resin, enabling the synthesis to be performed by undergraduate organic chemistry students. This synthesis lab was successfully completed within one 4-h session by second-year students. The procedures are relatively inexpensive and versatile, enabling modifications to generate a variety of oligomer sequences from commercially available reagents including bromoacetic acid and a diverse set of primary amines.

Original languageEnglish (US)
Pages (from-to)637-639
Number of pages3
JournalJournal of Chemical Education
Volume87
Issue number6
DOIs
StatePublished - 2010

Fingerprint

Peptidomimetics
Oligomers
N-substituted Glycines
Peptoids
Students
chemistry
student
drug
Amines
Resins

Keywords

  • Combinatorial chemistry
  • Drugs/pharmaceuticals
  • Hands-on learning/manipulatives
  • HPLC
  • Laboratory instruction
  • Mass spectrometry
  • Medicinal chemistry
  • Nucleophilic substitution
  • Organic chemistry
  • Proteins/peptides
  • Second-year undergraduate
  • Synthesis
  • Thin layer chromatography

ASJC Scopus subject areas

  • Chemistry(all)
  • Education

Cite this

Rapid multistep synthesis of a bioactive peptidomimetic oligomer for the undergraduate laboratory. / Utku, Yeliz; Rohatgi, Abhinav; Yoo, Barney; Kirshenbaum, Kent; Zuckermann, Ronald N.; Pohl, Nicola L.

In: Journal of Chemical Education, Vol. 87, No. 6, 2010, p. 637-639.

Research output: Contribution to journalArticle

Utku, Yeliz ; Rohatgi, Abhinav ; Yoo, Barney ; Kirshenbaum, Kent ; Zuckermann, Ronald N. ; Pohl, Nicola L. / Rapid multistep synthesis of a bioactive peptidomimetic oligomer for the undergraduate laboratory. In: Journal of Chemical Education. 2010 ; Vol. 87, No. 6. pp. 637-639.
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