A Discovery-Oriented Approach to Solid-Phase Peptide Synthesis

Brian B. Brennan, Matthew R. Bockman, Christopher J. Miedema

Research output: Journal ArticleArticlepeer-review

Abstract

In this discovery-oriented laboratory experiment, students use solid-phase synthesis techniques to construct a dipeptide containing an unknown amino acid. Following synthesis and cleavage from the polymeric support, electrospray ionization-mass spectrometry is employed to identify the unknown amino acid that was used in the peptide coupling. This experiment, performed in two, 3-h laboratory periods, provides an opportunity for students to learn the technique of solid-phase peptide synthesis and to critically evaluate data that they generate in the laboratory. The experiment is suitable for second-semester organic chemistry students as they learn methods for the formation of amide bonds or upper-level biochemistry students as they learn about the primary structures of proteins.
Original languageAmerican English
JournalJournal of Chemical Education
Volume89
StatePublished - Oct 9 2012

Keywords

  • Second-Year Undergraduate
  • Upper-Division Undergraduate
  • Laboratory Instruction
  • Biochemistry
  • Organic Chemistry
  • Hands-On Learning/Manipulatives
  • Amino Acids
  • Bioorganic Chemistry
  • Mass Spectrometry
  • Synthesis.

Disciplines

  • Chemistry
  • Organic Chemistry

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