Undergraduate Honors Theses

Thesis Defended

Fall 2017

Document Type

Thesis

Type of Thesis

Departmental Honors

Department

Chemistry & Biochemistry

First Advisor

Maciej A. Walczak, Ph.D: Department of Chemistry and Biochemistry

Second Advisor

Jeffery C. Cameron, Ph.D: Department of Chemistry and Biochemistry

Third Advisor

Tarek Sammakia, Ph.D: Department of Chemistry and Biochemistry

Fourth Advisor

Charles Rodgers, Ph.D: Department of Physics

Abstract

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.

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