Comparison of dissociation tendencies of meta- & paratrifluorotolylglycine methyl esters and meta- & paratolylglycine methyl esters in ESI-MS

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Kerstetter, Dale R.
Vu, Anthony
Graichen, Adam
Vachet, Richard
Tokunboh, Idia
Van Stipdonk, Michael J.

Kerstetter, Dale, Vu, Anthony, Graichen, Adam, Vachet, Richard, Tokunboh, Idia and Mike Van Stipdonk(2009) .Comparison of Dissociation Tendencies of Meta- & Para trifluorotolylglycine Methyl Esters and Meta-& Para-tolylglycine Methyl Esters in ESI-MS . In Proceedings: 5th Annual Symposium: Graduate Research and Scholarly Projects. Wichita, KS: Wichita State University, p. 124-125


Peptide fragmentation is an integral part of an evolving field commonly referred to as proteomics. Understanding of peptide fragmentation is vital to continued proteomic research. The frame work of this study was the benzylglycine methyl ester with either a methyl or trifluoromethyl constituent in the para- and meta-positions of the benzyl ring. The glycine methyl ester was coupled to the different acids using a PS-carbodiimide resin. The acids used were p-trifluorotoluic acid, m-trifluorotoluic acid, p-toluic acid, and m-toluic acid. Synthesis was confirmed using electrospray ionization mass spectrometry (ESI-MS). Collision induced dissociation (CID) was utilized to observe the dissociation tendencies of the given molecules. The anticipated b2 + pathway as seen in previous studies was not as readily seen for some of the molecules in this study. Density functional theory calculations were employed for the reaction pathways to determine the thermodynamic characteristics on the pathways to help explain the observed fragmentation pathways. underserved and primary care settings.

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Paper presented to the 5th Annual Symposium on Graduate Research and Scholarly Projects (GRASP) held at the Hughes Metropolitan Complex, Wichita State University, May 1, 2009.
Research completed at Department of Chemistry College of Liberal Arts & Sciences