Synthesis and structural characterization of amide-linked derivatives of N-acetyl neuraminic acid
AuthorGregar, Travis Quinton
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PublisherThe University of Arizona.
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AbstractAmide linked carbohydrates represent a tremendously different type of compound. Sugars have traditionally been linked together as either N or O linked via the anomeric carbon to make larger compounds, i.e. Sialyl Lewis X. This linkage leads to great instability under acidic and biological conditions. N-Acetyl neuraminic acid is a naturally occurring delta peptide. Colominic acid is the naturally occurring O linked polymer of N-acetyl neuraminic acid. This polymer has been found to possess a helical structure starting at the hexamer length. Changing from an O linkage to an amide linkage provides much greater stability under various conditions, including acidic and biological. Various derivatives of N-acetyl neuraminic acid have been synthesized and linked together via an amide linkage. Experiments including NH/ND exchange and circular dichroism has given strong evidence indicating there is some type of ordered secondary structure. Proving the existence of secondary structure is extremely difficult. Techniques traditionally used in the area of peptide chemistry to elucidate secondary structure cannot be directly applied to this system. Various techniques will be used and evidence presented to support the formation of secondary structure.
Degree ProgramGraduate College