Date of Award

Fall 12-2021

Document Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry & Biochemistry

Program/Concentration

Chemistry

Committee Director

Guijun Wang

Committee Member

James Lee

Committee Member

Erin Purcell

Committee Member

Bala Ramjee

Committee Member

Joshua Choi

Abstract

Functional glycoconjugates are important classes of compounds with many applications in different research fields. Our lab has been studying the synthesis and applications of different classes of glycoconjugates ranging from macrocycles to sugar heterocycle derivatives. Due to the importance of these compounds, our research is based on development of synthetic methods for various carbohydrate derivatives. This dissertation includes introduction and overview of projects, followed by the synthesis and studies of several different series of glycomacrolactones. The second project focuses on two classes of photoresponsive molecules, the coumarins and diarylethenes. The third project involves the synthesis and self-assembling properties of isoxazole-based glycoconjugates.

Macrocycles are important compounds for drug discovery and development. They are also useful in supramolecular chemistry and materials science. Using the copper catalyzed azide alkyne cycloaddition reactions (CuAACs), “click chemistry”, several glycomacrocycles have been synthesized previously. Here the synthesis and characterization of two new series of glycomacrolatones are reported. The methods for effective macrolactonization steps were established and the synthesized macrolactones were analyzed for applications in molecular recognition and catalysis.

In the third chapter, to expand the research into obtaining functional new materials, two classes of photo-responsive compounds are studied. The first class focuses on coumarin derivatives, which showed fluorescent properties and can be used as fluorescent probes for biomedical research. Using a sugar gelator template, several sugar-coumarin derivatives were shown to be effective low molecular weight gelators (LMWGs). The second class involves the diarylethene based photochromic molecules, which can be used as molecular switches for a variety of applications including optical memory devices. The preparation of diarylethene derivatives is discussed, their applications in hybrid optical materials are being studied through collaboration.

Besides the coumarin-sugar conjugates and glycosyl triazole derivatives, using the demonstrated carbohydrate building blocks, we have also synthesized and characterized a new series of glycosyl isoxazole derivatives. The current study focuses on the synthetic method and the preliminary gelation properties of these sugar heterocycle derivatives. These compounds are expected to have utilities in various research fields, which will be further explored in the future.

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DOI

10.25777/fxt2-t966

ISBN

9798780600800

ORCID

0000-0001-7638-2699

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