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Permanent link (DOI): https://doi.org/10.7939/R3W37M

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Synthesis of polyacetylene glycosides and thioglycosides Open Access

Descriptions

Other title
Subject/Keyword
thioglycosides
polyacetylene
glycosides
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Pan, Yanqing
Supervisor and department
Todd L. Lowary (chemistry)
Rik R. Tykwinski (Chemistry)
Examining committee member and department
David R. Bundle (Chemistry)
Gregory G. Goss (Biological Science)
Department
Department of Chemistry
Specialization

Date accepted
2009-10-01T16:30:07Z
Graduation date
2009-11
Degree
Master of Science
Degree level
Master's
Abstract
Polyacetylene glycosides are natural products isolated from a variety of natural sources, primarily terrestrial plants and fungi. Polyacetylene glycosides isolated to date feature a linear and conjugated polyacetylene chain and a mono di-, or trisaccharide group in their structures. These compounds have been shown to possess a host of different biological activities, including anti-inflammatory effects, inhibition of nitric oxide production and histamine release, anti-bacterial activity, and the ability to inhibit the enzyme 12-lipoxygenase. The project described in this thesis focuses on polyacetylene glycosides and polyacetylene thioglycosides by glycosylating or thioglycosylating mono-, di-, or triyne alcohols, which have been synthesized using the Cadiot-Chodkiewicz reaction and Fritcsh-Buttenberg-Wiechell rearrangement. Twenty-seven polyacetylene glycosides and thioglycosides have been synthesized. Given the structural similarity of these compounds to bioactive natural products, we expected the molecules should have interesting biological activities. Thirty compounds have thus been assayed for cytotoxicity against MCF-7 breast lines, as well as anti-bacterial activity.
Language
English
DOI
doi:10.7939/R3W37M
Rights
License granted by Yanqing Pan (ypan@ualberta.ca) on 2009-09-26T22:47:48Z (GMT): Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of the above terms. The author reserves all other publication and other rights in association with the copyright in the thesis, and except as herein provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
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