Event Title

NMR Study of Hydroxymethylfurfural (HMF) Reactivity toward Nucleosides of DNA

Presenter Information

Cameron Hovey, Minnesota State University, Mankato

Location

CSU 253/4/5

Start Date

4-4-2011 11:00 AM

End Date

4-4-2011 12:30 PM

Student's Major

Chemistry and Geology

Student's College

Science, Engineering and Technology

Mentor's Name

Danae Quirk Dorr

Mentor's Department

Chemistry and Geology

Mentor's College

Science, Engineering and Technology

Description

Hydroxymethylfurfural (HMF) is an α,β-unsaturated aldehyde (enal) derived from the dehydration of sugars, notably fructose. HMF is commonly formed in high-fructose corn syrup—a staple ingredient in modern-day food and beverages, among other things—due to heating during storage. Past research involving other enals, such as crotonaldehyde and acrolein, has shown that their bifunctional character enables them to form covalent bonds with 2 nucleotides within DNA simultaneously, forming a cross-link. In order to investigate the potential reactivity of HMF toward DNA, HMF was allowed to react with isolated samples of adenosine, thymidine, cytidine, and guanosine, the four distinct nucleoside building blocks contained in DNA. The resulting products were then examined using NMR spectroscopy to explore their corresponding chemical structures. The NMR spectra were indicative of whether or not a reaction occurred, bonding HMF to a respective nucleoside to generate a new molecule.