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John D. Spence |
Courses Taught:
Chem 2319 Organic
Chemistry
Chem 1119 Lab Methods in Organic Chemistry
Chem 2320 Organic & Bioorganic
Chemistry Chem 2220 Chemical
Synthesis I
Chem 4347 Supramolecular
Chemistry
Chem 3221 Chemical Synthesis II
My primary teaching duties are in the organic sequence, Chemistry 2319 and 2320, along with the associated laboratory courses Chemistry 1119 and 2220. At Trinity the organic sequence begins in the second semester of the students first year and concludes in the fall of their second year of college. The second semester course, organic and bioorganic chemistry, contains a heavy emphasis on the chemistry of biological molecules. This includes a study of the traditional second semester topics covering carbohydrates, lipids, amino acids and peptides and nucleic acids. In addition a good deal of metabolism and mechanistic bioorganic chemistry of these molecules are covered in the course. Nearly one-third of the course covers bioorganic chemistry.
In the laboratory courses the first semester organic lab, Chemistry 1119, is an introductory course that teaches students basic techniques in experimental organic chemistry. The second semester course, Chemistry 2220, is anything but an introductory course. The synthesis I lab focuses on synthetic organic chemistry and spectroscopic analysis of products. In this lab students are given unique starting materials for standard organic reactions such as Friedel-Crafts Acylation, Aldol Condensation and Grignard reactions. The idea behind each student receiving a unique starting material is for them to work on a project that is similar to other students but contains unique observations and data such as product appearance, mp, bp, 1H NMR, IR and GC. This forces the student to become independent in the lab as well as their analysis and gives them the opportunity to work with real data from their individual experiment.
Research in my group is centered around the synthesis and properties of macrocycles related to porphyrins, calixarenes and the enediyne anti-tumor antibiotics. We are currently developing synthetic strategies to utilize porphyrin macrocycles to deliver and activate enediyne pro-drugs towards Bergman cyclization. The connection of a porphyrin macrocycle with an enediyne pro-drug, generating a family of compounds we refer to as porphyrenediynes, introduces a number of advantages for drug delivery such as water solubility, DNA binding, tumor selectivity and improved photo-activation through porphyrin substitution. We are also interested in fine-tuning the properties of calixarenes by developing synthetic methods to systematically replace the bridging carbon atoms with nitrogen atoms. This substitution can have a profound effect on the electronic and physical properties of the macrocycle and offer new motifs for functionalization. Some of the compounds we are working on in the laboratory are shown below. For a complete description of these research projects see our research group page.
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