Title

Synthesis of Benzophenone-O-Glycosides under Basic Conditions

Document Type

Book

Authors

Samuel Burns, University of Minnesota - MorrisFollow

Files

Description

Type 2 diabetes is a growing health concern worldwide characterized by high blood sugar. Anti-diabetic therapy aims at correcting this sugar imbalance by inhibiting the enzyme α-glucosidase which is responsible for cleaving carbohydrates and starch into glucose. Benzophenone glycosides are a class of biomolecules with α-glucosidase inhibitory properties that have garnered some attention. It can be found and isolated from some traditional medicinal plants which was not done for this project. Once isolated, new derivatives can be synthesized by manipulating protecting groups of the starting material to get the benzophenone. The benzophenone can then undergo glycosylation with the protected sugar to get the penultimate benzophenone glycoside. This process can be monitored using TLC plates and the final product characterized using NMR and TLC. In lab glucose and galactose were used as the starting material and were reacted with the 2-hydroxybenzophenone and 2-hydroxy-4 methoxybenzophenone. TLC plates were then used to identify the fraction that contained both the spots for the sugar and benzophenone. This fraction could then be used in the NMR to confirm the presence of the coupling peaks in the C¹³ NMR as well as the correct ratio of peaks belonging to the sugar and benzophenone to confirm the sugar and benzophenone were successfully coupled.

Publication Date

4-21-2022

Keywords

Type 2 diabetes; Glycosides--Synthesis

Disciplines

Medicinal-Pharmaceutical Chemistry

Comments

Adviser: Alyssa Pirinelli

Recommended Citation

Burns, Samuel, "Synthesis of Benzophenone-O-Glycosides under Basic Conditions" (2022). Undergraduate Research Symposium 2022. 3.
https://digitalcommons.morris.umn.edu/urs_2022/3

Primo Type

Conference Proceeding