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Liquid chromatography-tandem mass spectrometry (LC-MS/MS) is a powerful analytical technique used in many disciplines. Therefore, teaching this technique in the undergraduate laboratory should involve practical data collection in a "real-world" application. For an upper division plant chemistry course, we developed a laboratory module of two experiments analyzing plant secondary metabolites in food and beverage products by LC-MS/MS. In the first, students use product ion scans and literature references to determine which chlorogenic acids (phenolic antioxidants), including which isomers, are present in coffee and hard cider. In the second experiment, students performed an untargeted analysis of peppercorn extract, examining the MS/MS fragmentation of the major alkamides (compounds responsible for pepper's pungency). Students then selected unknown alkamides, performed product ion scans, and proposed structures based on the observed fragments and losses. These experiments emphasize the utility of MS/MS for distinguishing closely related compounds, for making qualitative comparisons, and for proposing structures of unknown compounds. Both a pretest/post-test assessment and laboratory reports were used to assess learning outcomes related to MS/MS.
Cinelli et al. (Wed,) studied this question.