As a prospective graduate student, I am interested in the field of organic chemistry, with a focus on the interfaces between total synthesis, medicinal chemistry, and chemical biology. I love studying synthetic chemistry and methodology, but I also want to make molecules and materials that have applications to a larger research goal. I have four years of undergraduate research experience, and the more time I spend in the lab the more I love it. The lifestyle and environment of being in graduate school doing research every day is exactly what I can picture myself doing for the next 5 years or more, and I enjoy being part of an academic research group so much that I hope to one day become a professor and lead my own group.
For the past four years I have worked as an undergraduate researcher at UC San Diego and The Scripps Research Institute. Independent research has taught me flexibility, innovation, and problem-solving skills. I have learned a great deal more by doing hands-on research than I have from strictly studying textbook material. During my years of independent undergraduate research, I have formulated synthetic routes from scratch and learned to troubleshoot problems as I encounter them. Most of my research experience has been in the lab of Dr. Nathan Gianneschi at UCSD, where I have worked since 2009. The hands-on experience I got in Nathan’s lab sparked my passion for research in organic chemistry, and my enthusiasm has only grown as I’ve become more independent in the lab. I have also worked in the laboratory of K. C. Nicolaou at the Scripps Research Institute. It was in the Nicolaou group where I learned a multitude of advanced synthetic techniques and where I discovered how much I enjoy synthetic chemistry. My experiences with hands-on research chemistry have been the most enjoyable parts of my college career, and I can’t wait to continue learning as part of a research group in graduate school.
As part of the Nicolaou group, I worked on the synthesis of a MRSA-active natural product antibiotic. My assignment was to independently design the synthesis of an isoxazole building block. The graduate students working on the project had one route to make the isoxazole, but only with 25% yield. Through many weeks of literature research and trial-and-error experiments, I found a shorter route to the isoxazole and also improved the overall yield to 80%. Since my scheme is now being used in the group’s overall synthesis, I will help write and be included in the publication when the total synthesis is finished.
During my time in the Gianneschi group, I have worked on multiple projects ranging from the synthesis of DNA- and polymer-based nanomaterials to small molecule synthesis. My main projects have been the synthesis of fluorescent and near-infrared dyes and their incorporation into DNA, peptides, and nanomaterials. Many commercial dyes and dye conjugates are expensive, so I devised economical and efficient ways to make them for the group myself. The first two dyes I developed synthetic routes for were fluorescein and tetramethylrhodamine (TAMRA), which I then coupled to a thymidine DNA base in order to make a fluorescent phosphoramidite for oligonucleotide labeling. Our group uses these phosphoramidites to study the morphology and reactivity of DNA-based nanomaterials with potential applications to drug delivery and biomedical imaging. My current project in the Gianneschi group deals with cyanine near-IR dyes. Cyanine dyes are especially expensive at around $1,000 per milligram. I successfully implemented syntheses of Cy5.5 and Cy7, and my process only costs $140 per gram in materials. While researching different ways to synthesize these dyes, I became curious about how to make them more efficient in terms of photostability, quantum yield, and Stokes shifts. I decided to study the effects of changing various parts of the cyanine dye structure by creating a collection of 17 different symmetric and asymmetric dyes and comparing the spectral properties of each. My work is ongoing, and while making a library of various dye compounds for use in our group’s nanomaterials studies, I hope to gain insight into the relationship between the structural details, reactivity, and spectral properties of cyanine dyes along with many new synthetic techniques.
During my graduate studies, I want to continue doing synthetic chemistry while gaining experience in other areas that I’ve had less exposure to like biological activity and mechanism of action studies of small molecules and natural products, chemoenzymatic methods in synthesis, combinatorial chemistry, and asymmetric catalysis and methodology. I want to learn and do as much as I can during my graduate studies to develop a diverse chemistry background and more importantly to find what interests me the most in order to develop a specialty that will eventually direct the future of my career and independent research.
