Document Type
Honors Thesis
Major
Chemistry
Advisor(s)
Matthew Brichacek
Committee Members
Melissa Ladenheim, Natalie Machamer
Graduation Year
May 2023
Publication Date
2025
Abstract
Glycans make up cell walls that allow for defense, energy metabolism and signaling. Within the classes of glycans is xylan, which is a major component of plant biomass and secondary cell walls. The prevalence of glycans in almost all plants makes them an abundant source of fuel for renewable energy. The primary impediment to utilizing xylan and cultivating the energy present in it is the inability to degrade the bonds present. Using a novel reagent, 4-MU Iodonium Triflate, we were able to synthesize 4-MU glycan probes. The chemical synthesis of the 4-MU probe commenced from amino- 4-MU in a two-step process including a Sandmeyer reaction and a subsequent substitution. The 4-MU reagent was synthesized at an approximate yield of 26% and then it was subsequently conjugated to a model glucan in 22% yield. The next focus was on improving the efficiency of 4-MU probe production and attaching it to other sugar groups, especially ones more structurally similar to xylan. In the future, these reactions, in conjunction with the 4-MU reagent, can be transferred to sustainability studies concerning biofuels.
Recommended Citation
Milligan, Mary, "Synthesis of a Novel Fluorescent Probe for Biomass Degradation" (2025). Honors College. 969.
https://digitalcommons.library.umaine.edu/honors/969