Document Type

Dissertation

Degree

Doctor of Philosophy

Major

Chemistry, Organic

Date of Defense

12-14-2013

Graduate Advisor

Alexei Demchenko, PhD

Committee

Prof. Alexei V. Demchenko

Prof. Rudolph E. K. Winter

Prof. Keith J. Stine

Prof. Eike Bauer

Abstract

Having multiple functions in biological systems e.g. fertilization, blood group determination, cell growth; carbohydrates have remained attractive subjects for the study. They are also involved in various life threatening biological processes, such as viral and bacterial infections, tumor development, etc. Understanding of these involvements/interactions of carbohydrates in such critical processes is essential for the development of carbohydrate based vaccines and therapeutics. Although carbohydrates are present abundantly in nature, their isolation is cumbersome and low yielding, which is why, the synthesis of carbohydrate units has been of interest to many scientists. Efforts have been made to make these synthetic methods more and more efficient with the primary focus on the yield and stereoselectivity of glycosylation reactions. Over the years, researchers have observed various factors that influence the outcome of the glycosylation reaction, most of which are dependent on the structure of two coupling components of the glycosylation reaction, i. e. the glycosyl donor and glycosyl acceptor. This topic also became the basis for this doctoral dissertation work wherein the study has been focused on the development of a new class of glycosyl donors and comparison of their properties with known compounds. The investigation of various leaving groups was conducted with a goal of obtaining glycosyl donors with tunable reactivity and studying the effect of various modifications on the outcome of glycosylation reactions.

OCLC Number

870969258

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