Novel nitric oxide donors and glycolipid biosensors

Date of Award




Degree Name

Doctor of Philosophy (Ph.D.)



First Committee Member

Peng George Wang - Committee Chair


In the human body nitric oxide (NO) is synthesized from L-Arginine by Nitric Oxide Synthase. NO plays key roles in biological systems: NO relaxes blood vessels, intervenes in immune system regulation processes and in the pathology of neurological diseases. This work describes the synthesis and characterization of several novel glyco-S-nitrosothiols capable of acting as selective NO donors. In vitro collaborative studies have shown potential for these compounds to specifically deliver NO to breast and prostate cancer cells. This selectivity is due to the enzymatic recognition of the sugars appended to these donors. Dephostatin inactivates homogeneous recombinant yersinia and mammalian protein tyrosine phosphatases (PTP). N-nitroso compounds (dephostatin analogs and other N-nitroso peptides) have been prepared and characterized. Attempts to synthesize several N-nitroso sulfonamides are presented. Several glycolipids have been synthesized which could be used to colorimetrically detect bacteria and viruses based on conformational changes in the lipid backbone upon binding of the pathogen to the sugar moiety. The synthesis of fluorescent biotinylated 2,6-diaminopyridine (BAP) is described along with its application in the fractionation of mono and oligosaccharides, and the formation of neoglycoproteins by coupling with avidin and streptavidin. Two unexpected transformations are reported: the first one was seen while treating mannose with hydrazine, and the second one was observed during the hydrogenation of 2,5-dinitrobenzamide. The latter is believed to be a new reaction.


Biology, Microbiology; Chemistry, Organic; Chemistry, Pharmaceutical

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