Solid-phase peptide synthesis and characterization in the undergraduate lab

CHED 73

Anthony J. Langione, ajl5001@psu.edu, Penn State, 4081 Carlisle Road, Dover, PA 17315, Ronald B. Davis Jr., ronaldd@american.edu, 132 Quincy Avenue, State College, PA 16801, and Katherine M. Masters, kmasters@psu.edu, Department of Chemistry, Penn State University, 210 Whitmore Lab, University Park, PA 16802.
The synthesis and characterization of a short peptide has been developed into an experiment for use in the undergraduate laboratory. Manual solid-phase synthesis of the tetrapeptide Ac-GYPG-NH2 is carried out by the students followed by characterization via NMR. In addition to learning the basics of solid-phase synthesis, the students are also introduced to conformational analysis of peptides using NOESY and 1H NMR techniques. The ratio of cis- and trans-proline isomers is determined by integration of the 1H NMR spectrum. Inter-residue NOESY cross peaks enable the students to visualize the tyrosine and proline side chain orientations in space for both the cis and trans conformations. This experiment has recently been implemented into the advanced undergraduate laboratory at Penn State's University Park campus and has proven very successful in its first year in the curriculum.
 

General Posters
7:30 PM-9:30 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Division of Chemical Education

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008