Persistent Link:
http://hdl.handle.net/10150/291822
Title:
Solution and solid-phase synthesis of sialooligomers
Author:
Nguyen, Can Phvoc, 1972-
Issue Date:
1998
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:
The solution phase synthesis of amide-linked derivatives of sialic acid has been achieved. The N-acetyl group on sialic acid was removed via N-BOC protection of the lactam and ensuing displacement with NaOMe. Subsequent removal of the BOC protecting group group with TFA resulted in the free amine which was then coupled with the free acid using BOP, Hunig's base, and NMP. These compounds may afford greater solubility than previously synthesized amide-linked carbohydrate amino acids and may give rise to novel helical structures. The efficacy of using monomer units of sialic acid in solid-phase oligomer synthesis has also been studied. The peracetylated FMOC-protected derivative of sialic acid which has been shown to be amenable to solid-phase synthesis has also been synthesized. However, difficulties were encountered during the solid-phase synthesis of these sialooligomers due to transacetylation of the acetate groups to re-form the N-acetyl bond.
Type:
text; Thesis-Reproduction (electronic)
Keywords:
Chemistry, Organic.
Degree Name:
M.S.
Degree Level:
masters
Degree Program:
Graduate College; Chemistry
Degree Grantor:
University of Arizona
Advisor:
Gervay, Jacquelyn

Full metadata record

DC FieldValue Language
dc.language.isoen_USen_US
dc.titleSolution and solid-phase synthesis of sialooligomersen_US
dc.creatorNguyen, Can Phvoc, 1972-en_US
dc.contributor.authorNguyen, Can Phvoc, 1972-en_US
dc.date.issued1998en_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.abstractThe solution phase synthesis of amide-linked derivatives of sialic acid has been achieved. The N-acetyl group on sialic acid was removed via N-BOC protection of the lactam and ensuing displacement with NaOMe. Subsequent removal of the BOC protecting group group with TFA resulted in the free amine which was then coupled with the free acid using BOP, Hunig's base, and NMP. These compounds may afford greater solubility than previously synthesized amide-linked carbohydrate amino acids and may give rise to novel helical structures. The efficacy of using monomer units of sialic acid in solid-phase oligomer synthesis has also been studied. The peracetylated FMOC-protected derivative of sialic acid which has been shown to be amenable to solid-phase synthesis has also been synthesized. However, difficulties were encountered during the solid-phase synthesis of these sialooligomers due to transacetylation of the acetate groups to re-form the N-acetyl bond.en_US
dc.typetexten_US
dc.typeThesis-Reproduction (electronic)en_US
dc.subjectChemistry, Organic.en_US
thesis.degree.nameM.S.en_US
thesis.degree.levelmastersen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.advisorGervay, Jacquelynen_US
dc.identifier.proquest1391067en_US
dc.identifier.bibrecord.b38830309en_US
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