Date Approved

6-19-2019

Embargo Period

8-1-2019

Document Type

Thesis

Degree Name

M.S. Pharmaceutical Sciences

Department

Chemistry and Biochemistry

College

College of Science & Mathematics

First Advisor

Ramanujachary, Kandalam

Second Advisor

Mugweru, Amos

Third Advisor

Jonnalagadda, Subash

Subject(s)

Nonnutritive sweeteners; Sucralose--Derivatives

Disciplines

Medicinal and Pharmaceutical Chemistry

Abstract

Sucralose is an artificial sugar substitute which is most commonly used sweetener among other artificial sweeteners. It is derived from sucrose through a complex chemical process that selectively substitutes three atoms of chlorine for three hydroxyl groups on sucrose molecule, which have shown some inhibition of bacterial growth in gut. The goal of the project was to substitute halide in sucralose in a way that it sustains potential anti-bacterial activity along with sweetening effect, which can be then incorporated into mouthwash formulation. Sucralose is very stable molecule and it also has other physico-chemical advantages which are suitable for our anticipated reactions. We initiated the modification of this chloro sugar starting from replacement by other halide molecule via SN2 nucleophilic reaction. Additionally, we also reacted different functional group for chlorine replacement which involved click chemistry. Use of azide ion increased the complexity of the molecule since it has three nitrogen which undergoes rearrangement. To produce the library of target molecules hydroxyl group was protected by acetate group and used as starting material for further reactions. The compounds synthesized were characterized by different analytical techniques which might be potential anti-bacterial agents.

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