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A Discovery-Oriented Approach to Solid-Phase Peptide Synthesis
Journal of Chemical Education (2012)
  • Brian B. Brennan, Illinois Wesleyan University
  • Matthew R. Bockman, Illinois Wesleyan University
  • Christopher J. Miedema, Illinois Wesleyan University
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.
  • Second-Year Undergraduate,
  • Upper-Division Undergraduate,
  • Laboratory Instruction,
  • Biochemistry,
  • Organic Chemistry,
  • Hands-On Learning/Manipulatives,
  • Amino Acids,
  • Bioorganic Chemistry,
  • Mass Spectrometry,
  • Synthesis.
Publication Date
October 9, 2012
Publisher Statement
The Journal of Chemical Education is published by The American Chemical Society and Division of Chemical Education, Inc.,
Citation Information
Brian B. Brennan, Matthew R. Bockman and Christopher J. Miedema. "A Discovery-Oriented Approach to Solid-Phase Peptide Synthesis" Journal of Chemical Education Vol. 89 Iss. 11 (2012)
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