Publication Date

Spring 2011

Degree Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry

Advisor

Marc d'Alarcao

Keywords

Diabetes, Hybrid inositol glycan analogues, Inositol glycans, Inositol phospho-glycan, Insulin-mimetic

Subject Areas

Chemistry; Biochemistry; Organic Chemistry

Abstract

Inositol glycans (IGs) are small oligosaccharides exhibiting insulin-like metabolic activities in insulin-sensitive cells. The signal transduction pathways activated by IGs in these cells are still under study, but it is known that there is cross talk between the IG-signaling pathway and the insulin-signaling pathway downstream of the insulin receptor. Therefore, IGs may have potential for use in the treatment of type II diabetes mellitus. However, natural IGs are heterogeneous and difficult to isolate. Hence, synthetic IGs and their analogues have been chemically synthesized and evaluated for insulin-mimetic properties by various research groups. Unfortunately, the most biologically active IG analogues are structurally complex and difficult to synthesize. The present work reports the progress towards designing and preparing biologically active IG analogues with short and relatively simple synthetic pathways. The strategy is to synthesize a small library of hybrid inositol glycan analogues (HIGAs) where each HIGA consists of an inositol core covalently tethered to a variety of readily available non-carbohydrate moieties. Synthesis of one such HIGA (compound 16) was successfully accomplished. Initial results from mass spectrometric analysis provide evidence of molecular mass of compound 16.

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