Synthesis and structural characterization of amide-linked derivatives of N-acetyl neuraminic acid

Persistent Link:
http://hdl.handle.net/10150/279827
Title:
Synthesis and structural characterization of amide-linked derivatives of N-acetyl neuraminic acid
Author:
Gregar, Travis Quinton
Issue Date:
2001
Publisher:
The University of Arizona.
Rights:
Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
Abstract:
Amide 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.
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Chemistry, Organic.
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Graduate College; Chemistry
Degree Grantor:
University of Arizona
Advisor:
Gervay-Hague, Jacquelyn

Full metadata record

DC FieldValue Language
dc.language.isoen_USen_US
dc.titleSynthesis and structural characterization of amide-linked derivatives of N-acetyl neuraminic aciden_US
dc.creatorGregar, Travis Quintonen_US
dc.contributor.authorGregar, Travis Quintonen_US
dc.date.issued2001en_US
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en_US
dc.description.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.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectChemistry, Organic.en_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.advisorGervay-Hague, Jacquelynen_US
dc.identifier.proquest3026555en_US
dc.identifier.bibrecord.b42177418en_US
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