Date of Award

5-9-2015

Degree Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Peng George Wang

Second Advisor

Alfons Baumstark

Third Advisor

Maged Henary

Fourth Advisor

Gangli Wang

Abstract

Polysaccharide isotopes are responsible for many pathophysiological responses and can elicit strong immune responses. The first two Chapters demonstrated the chemical synthesis of a conserved and all α–linked Escherichia coli R3 outer core pentasaccharide. This pentasaccharide was conjugated to carrier protein (CRM197) through a propyl amino linker at the reducing end. An immunological analysis demonstrated that this glycoconjugate can elicit specific anti-pentasaccharide antibodies with in vitro bactericidal activity. In Chapter three, a Core Synthesis/ Enzymatic Extension (CSEE) technique for building a comprehensive O-glycan library was proposed. Furthermore, a highly efficient and convergent methodology was designed to synthesize all eight O-glycan core structures in large scale. These two emerging techniques have great potential to enable the investigation of structure-activity relationship between glycans and receptor proteins, thus facilitating the identification of biomedically important glycan isotopes.

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