Chemistry

The Wagner-Jauregg reaction is a powerful, yet largely unexplored organic reaction. This reaction pathway is a specialized type of Diels-Alder reaction that facilitates the formation of large, complex ring structures. This reaction is particularly impactful in synthetic chemistry due to the use of inexpensive and readily available starting materials to create more complex molecules. The Wagner-Jauregg reaction yields two primary products: the double Diels-Alder product and the ene product.

Cancer starts at a molecular level, when multiple mutations within the DNA of a cell cause uncontrolled cellular division without triggering apoptosis, or scheduled cell death. Pharmaceutical companies have developed chemotherapeutics that stop cancer by using molecules called intercalators to target DNA directly. Intercalators are small, planar molecules that force themselves between DNA base pairs, warping the tightly coiled double helix until it breaks.

This research focused primarily on the degradation of methyl orange through electrochemical methods. Methyl orange is one of many dyes belonging to a wider class of brightly colored dyes known as azo dyes. The defining factor of all azo dyes is the presence of a nitrogen-nitrogen double bond, also known as an azo bond. These dyes comprise up to 70% of all textile dyes used and are often released into water systems as waste. Such pollution lends itself to a variety of concerns including ecosystem disruption, such as eutrophication, and bodily harm.

Acridine dyes are commonly used for DNA-drug interaction studies because their polycyclic, planar, and aromatic structures can intercalate between adjacent DNA bases, stopping transcription and serving as potential chemotherapeutic agents. In my research, I have prepared a number of acridine derivatives to understand DNA-ligand interactions and structure-activity relationships better.

Although they are challenging to see with the naked eye, zooplankton do serve a vital role in an ecosystem. More specifically, we focused on copepods and the nature of their appearance. The pigment that contributes to their coloration is astaxanthin, the purpose of which is possibly for UV protection. We wanted to see how the levels of this pigment related to the location, as well as the time of the year of sampling. It was also important to be able to create a reproducible method for the extraction of astaxanthin, in order to prevent the wasting of material.

My research this summer studied a portion of the morphine molecule using the Wagner-Jauregg reaction. The final goal of this research is to use the Wagner-Jauregg reaction to synthesize a morphine-like molecule, that could have reduced addictive properties and allow people to use morphine without the risk of addiction. The Wagner-Jauregg reaction involves a double Diels-Alder reaction between a diene and dienophile. This reaction allows us to use cheaper and readily available molecules to synthesize more complex molecules, such as morphine.

My research project this summer, titled “Examining the Wagner-Jauregg Reaction: Providing an Alternative to Morphine,” was designed to explore the possibility of synthesizing a molecule similar to morphine, but without the addictive qualities. Through my research, I looked at known chemical reactions that might provide a pathway to forming a morphine-like molecule and explored ways to change and increase the effectiveness of those reactions. My project built off of the research of several students that studied at St. Lawrence in the past, as well as Dr.

Cancer is caused by cellular malfunction resulting in unchecked cell growth. When cells grow uncontrollably, they can crowd out nearby cells and spread to other parts of the body. The major cause of cancer is gene mutations, often caused by external carcinogens, which alter the DNA and other biological machinery required to keep our cell growth balanced.  Many cancers are hard to treat, and researchers are still trying to find selective anticancer drugs with mild or no side effects.

To combat the environmental and health issue of plastic pollution, we are looking to find a degradation process for plastics. There is a known microorganism phanerochaete chrysosporium that has the ability to degrade PET plastic. We used the enzyme that gives the microorganism this property as a basis for our proposed catalysts. To create the catalyst three different metals; Zinc (Zn), Iron (Fe), and Manganese (Mn) were used to metallate meso Tetra (4-carboxyphenyl) porphyrin (TCPP).

 Exposed to the elements, plastic degrades into smaller pieces known as microplastics and nanoplastics.1 These pieces have been found in our terrestrial, aquatic, and atmospheric environment, contaminating our food, water, and air.2 To mitigate this problem, we attempted to synthesize a copper cage that will theoretically break down the plastic to benign monomers of water and carbon. 3

This project intended to proposing a well-founded and viable total synthesis of a recently isolated natural product molecule. This molecule is structural challenging and interesting, and it has been tested to be potentially antibacterial. Thus, it is important for us to discover a synthetic route of this molecule. During the eight weeks of this summer (2020), we analyzed the structure of this molecule theoretically, and proposed a well-founded synthetic route of this molecule.

The reviewed mechanism, kinetics, and thermodynamics of proton-coupled electron transfer reactions work as the basis for electrochemical degradation of azo-dye. Cyclic voltammetry is applied for the electrochemical studies of this project. A review of metal-organic frameworks and their synthetic routes helps to design better catalysts work for degradation reaction.

TNT is both toxic and explosive, the detection of TNT represents an environmental and security concern. Dogs are often used for detection, but other methods are needed. This research project originally intended to understand how Ruthenium based TNT sensors function by discovering the mechanism by which Ruthenium’s fluorescence is quenched by TNT. Due to the nature of the summer, majority of my time was spent doing a literature review of previous TNT sensors.

The properties of the binding pathways of intercalating chemotherapy drugs to DNA were studied through literature search and data analysis. The transcription and replication of DNA are key steps to the deadliness of uncontrolled cellular division, or cancer. Characterization of the kinetic properties of the “intercalation” mechanism, the mysterious pathway by which some chemotherapy drugs are capable of halting DNA’s transcription and replication, is where I conducted extensive reading and data analysis this summer.

Due to the current challenges of the world, learning through videos is a crucial part of class preparation. Educational videos offer students an opportunity to learn in a safe environment. They are unique in their ability to allow students to see something first hand but are accessible from anywhere. The goal of this project is to create a series of organic chemistry lab tutorials. This will allow students to view the videos from home and come into the lab with a better understanding of what they are meant to be doing.

Many lives have been impacted ever since the first-time novel corona virus was observed in Wuhan on December 2019. With 5,403,218 confirmed cases of patients who have contracted COVID-19 as of 8/16/2020 along with 170,052 deaths in the United States; it remains vital to understand prevention and advance general public health against COVID-19 as well as progress in finding potential treatments. (Johns Hopkins Resource, 2020) Similarly, on March 13th, 2020 St. Lawrence University transitioned from in-person to online learning in attempt to facilitate social distancing and self-isolation.