Synthesis and Characterization of N-acetyl-glucosamine Based Macrocycles by SN2 Reactions

Title

Synthesis and Characterization of N-acetyl-glucosamine Based Macrocycles by SN2 Reactions

College

College of Sciences

Program

Ph.D. Chemistry

Publication Date

3-28-2019

Abstract

Macrocycles are a special class of molecules that exhibit unique properties due to their defined shape and conformation. They often are important compounds for drug discovery and development and have interesting applications in supramolecular chemistry and materials sciences. Using monosaccharides as the template, we can selectively functionalize at different positions of the sugar ring to afford regioselective derivatives that are suitable for macrocyclizations. Recently, our group have designed and synthesized a series of bis-triazole embedded glycomacrocycles utilizing the copper catalyzed azide alkyne cycloaddition reactions (CuAACs), click chemistry as the ring-closing step from readily available N-acetyl-D-glucosamine. In this research, we first utilized click chemistry to install functional groups that are suitable for intramolecular cyclization reaction. Through nucleophilic substitution reaction of carboxylic acid or hydroxyl functional groups introduced at the anomeric position and various leaving groups installed at the 6-position, we have synthesized several macrolactones and other macrocycles. The leaving group effect using different types of sulfonates in the macrolactonization step was evaluated. The detailed synthesis and applications of these novel glycomacrolactones will be discussed.

Files

Synthesis and Characterization of N-acetyl-glucosamine Based Macrocycles by SN2 Reactions


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