C. Eric Ballard

Two projects are currently active in Ballard's research group.

1. A Laboratory Sequence Linking Organic Chemistry II and Biochemistry Laboratory Courses
This project is conducted in collaboration with Scott Witherow, a faculty member in the department whose expertise includes biochemistry and biochemistry education.

The objective of this experiment is to help break down the perceived silos between these two classes by designing and implementing a sequence that spans them. Current Biochemistry Laboratory (CHE 320L) students focus on a semester-long sequence that includes expression, purification and kinetic studies of the enzyme alkaline phosphatase.

The kinetic studies include the use of inhibitors to study their effects. The extension offered by this project is to add an experiment to Organic Chemistry II Laboratory (CHE 235L) that prepares potential inhibitors of the enzyme by derivatizing the amino acid phenylalanine. It is envisioned that the same student could prepare a derivative in CHE 235L during one semester and study it as a potential enzyme inhibitor in CHE 320L during the following semester.

Ballard's group is preparing several categories of derivatives to determine the optimal one for the project. This project might serve as an introduction to research in Ballard's group.

Fig 1:Derivatization of phenylalanine to form a potential inhibitor.

Fig 2:Transformation of a 2-nitroarylacetylene into a 2-substituted indole.

2. Preparation of a Modified Indole Structure Using Two Chemical Reactions in One Flask
This project focuses on preparation of modified forms of indole. The indole core is present in many biologically active molecules, including the amino acid tryptophan, the neurotransmitter serotonin, the hormone melatonin, and the psychedelic drug psilocybin. Because of their interesting biological effects, several methods have been discovered for synthesizing compounds with the indole core.3 However, the investigation of new methods is still warranted.

This project aims to probe the preparation of one category of indole-based compounds (2-substituted indoles) using a cascade approach of two reactions occurring sequentially in the same reaction vessel. Similar approaches are known using expensive and/or toxic catalysts;4 this approach is different because it will probe the effects of inexpensive chemicals of low toxicity, such as those based on iron, zinc, or boron. This project lies in the area of green chemistry because it involves the use of safer catalysts and/or safer solvents.

This project is appropriate for students interested in a multi-semester project in discovery of synthetic organic methods.

Works Cited
1. Witherow, D.S. "A Ten-Week Biochemistry Lab Project Studying Wild-Type and Mutant Bacterial Alkaline Phosphatase," Biochem. Mol. Biol. Educ. 2016, 44, 555-564.
2. Dean, R. L. "Kinetic Studies with Alkaline Phosphatase in the Presence and Absence of Inhibitors and Divalent Cations," Biochem. Mol. Biol. Educ. 2002, 30, 401-407.
3. Lead reference: Sundberg, R. J., Ed. Indoles, 1996.
4. Lead reference: Yamane, Y.; Liu, X.; Hamasaki, A.; Ishida, T.; Haruta, M.; Yokoyama, T.; Tokyunaga, M. "One-Pot Synthesis of Indoles and Aniline Derivatives from Nitroarenes Under Hydrogenation Condition with Supported Gold Nanoparticles," Org. Lett. 2009, 11, 5162-5165.

Undergraduate research adds to the knowledge in a particular field. It is also another form of teaching. Students learn about science in their courses; they learn more about doing science during research experiences. In my group students can participate in all steps of a scientific project: reading the background literature to understand the scientific problem, developing a hypothesis related to it, designing appropriate experiments to test the hypothesis, learning bench techniques to execute the experiment safely and effectively, analyzing the data ethically, and drawing evidence-based conclusions. Students also learn how to share data in the form of poster presentations and/or written reports. Students may have an opportunity to present at the CNHS Undergraduate Research Symposium or at an external scientific conference or even to earn coauthorship on a publication.

University funds may be available to support research activities and/or travel to scientific conferences.

Fig 3: A student in Eric Ballard's group presents his research at a poster session.

(Undergraduate co-authors in bold type. *Corresponding author.)

Ballard, C. E.* "Lewis Acid-Catalyzed Hydrolysis of Cyclohexene Oxide," Submitted.

Ballard, C. E.* “Green Oxidative Homocoupling of 1-Methylimidazole,” J. Chem. Educ. 2013, 90, 1368-1372. http://pubs.acs.org/doi/abs/10.1021/ed200890f

Ballard, C. E.* “Green Reductive Homocoupling of Bromobenzene," J. Chem. Educ. 2011, 88, 1148-1151. http://pubs.acs.org/doi/abs/10.1021/ed100945h

Ballard, C. E.* "pH-Controlled Oxidation of an Aromatic Ketone: Structural Elucidation of the Products of Two Green Chemical Reactions," J. Chem. Educ. 2010, 87, 190-193. http://pubs.acs.org/doi/abs/10.1021/ed800054s

(Undergraduate co-authors in bold type. Presenting author(s) underlined.)

Grossman, B. C.; Ambrose, E. A.; Repke, L. A.; Ciesla, C. D.; Ballard, C. E.; Witherow, D. S.* "Designing an Experimental Sequence Linking Organic Chemistry II and Biochemistry Laboratories," Discover BMB, Seattle, WA, March 25-28, 2023.

Galili, T. and Ballard, C. E. "SN1 Alkylation of 1, 3-Dicarbonyl Compounds in Aqueous Reaction Mixtures," Poster at the 257th National ACS Meeting, March 31-April 4, 2019. CHED-1263.

Lundy, F. H. and Ballard, C.E. "SN1 Alkylation of Heterocycles in Aqueous Reaction Mixtures," Poster at the 257th National ACS Meeting, March 31-April 4, 2019. CHED-1201.

Ballard, C. E. "SN1 Alkylation of C-Nucleophiles in Aqueous Mixtures: Effect of Surfactant," Poster at the 255th National ACS Meeting, March 18-22, 2018. ORGN-690.

Ballard, C. E. "One-Pot Reduction/Cyclization of (2-Nitropheny)acetylenes to Prepare Indoles," Poster at the 245th National ACS Meeting, April 7-11, 2013. ORGN-840.