Type of Thesis
Chemistry & Biochemistry
Maciej A. Walczak, Ph.D: Department of Chemistry and Biochemistry
Jeffery C. Cameron, Ph.D: Department of Chemistry and Biochemistry
Tarek Sammakia, Ph.D: Department of Chemistry and Biochemistry
Charles Rodgers, Ph.D: Department of Physics
The investigation sought to determine whether a transition metal coupling reaction with aryl halides could be utilized to form glycoconjugates, carbohydrate-containing molecules, specifically C-Aryl Glycosides. Our successful novel application in glycochemistry employs the Stille coupling reaction and improves the viability of accessing a range of glycogonjugates for biological and therapeutic screening.(1) The reaction maintains exceptional retention of configuration from the carbohydrate-metal bond in the completed sp3 carbon – sp2 carbon bond of the produced glycoside. A synthesized library of C-aryl Glycosides was established utilizing this methodology; from which a selective schema was submitted for publication. This technology provides a route to discrete carbohydrate building blocks that can be assembled with minimal reagents and moderate synthetic knowledge. These building blocks can then be stereo-specifically attached to molecules of interest under a set of general catalytic conditions; expediting the investigation of carbohydrate’s role in biochemical processes that was limited by substrate dependent laborious processes of glycoconjugate formation.
Rourke, Michael, "The Synthesis Of Stannylated C1 Nucleophilic Monosaccharides For Use In The Stille Coupling Reaction" (2017). Undergraduate Honors Theses. 1524.