Honors Theses

Date of Award


Document Type

Undergraduate Thesis

Degree Name




Faculty Mentor

Marie Migaud


Juan Mata, David Forbes


Energy metabolism is complex, and NAD, or nicotinamide adenine dinucleotide, plays a huge role as an organic redox cofactor, driving metabolic reactions. The abundance of pathways dependent on NAD has led to an increase in the studies of NAD and its precursors. As a result NR, or nicotinamide riboside, is now a popular pharmaceutical taken to increase levels of NAD in the body. NR is not only a precursor to NAD, but a metabolite that is found in extracellular regions such as urine and blood. While this molecule should be an intracellular molecule, the fact that it is found in extracellular regions using LCMS indicates that this unknown peak may not represent NR. However, isomers of NR, such as the 2’-deoxy-PYR, also known as the 2’-deoxy-pyridone riboside, could be responsible for this unknown peak. The 2’-deoxy-PYR is formed due to the hyper-oxidation of NAD. The 2’-deoxy-PYR molecules, specifically where the oxidation takes place at the 2, 4, and 6 position on the nicotinamide base, are not known and have not been successfully synthesized. Due to the molecules structure, it is hypothesized that the 2’-deoxy-PYR species could be a substrate for DNA polymerase, possibly introducing mutations into healthy DNA. Because the 2’-deoxy-PYR species is potentially biologically relevant, in order to test if these species are actually present in biological specimens, the synthesis of these molecules are of the utmost importance. Ultimately, the synthesis of the 2’-deoxy-PYR isomers was explored using glycosidic chemistry, in order to characterize this molecule through analytical techniques as well as investigate its presence in the human body. The development of the methods as well as the synthesis of the 2’-deoxy-PYRMP were also investigated for the same purpose.

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