Publication Date

Spring 2010

Degree Type


Degree Name

Master of Science (MS)




Marc d'Alarcao


Apoptosis, Cancer, Inositol glycans, Insulin signaling

Subject Areas

Chemistry, Organic; Chemistry, Biochemistry


Inositol glycans (IGs) are naturally occurring oligosaccharides that can stimulate insulin sensitive cells. Several synthetic IG analogues have been shown to activate the insulin-signaling pathway, including the stimulation of the enzyme pyruvate dehydrogenase (PDH) phosphatase that can further stimulate aerobic metabolism in cells. Cancer cells shift to anaerobic metabolism in order to escape intrinsic apoptosis (Warburg Effect). IG's ability to stimulate aerobic metabolism might provide a method to reverse the Warburg Effect and thereby induce apoptosis in the cancer cells. One specific palmitoylated IG analogue has been shown to selectively kill cancer cells while having no adverse effect on normal cells. However, this analogue is unstable under physiological conditions due to ester hydrolysis and acyl group migration.

This thesis describes the work on the synthesis of an IG analogue in which the ester linkage has been replaced by ether. Since ethers are comparatively more stable than esters, the resulting IG analogue should be more stable than the parent analogue. Biological activity of this IG analogue will be reported elsewher