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Permanent link (DOI): https://doi.org/10.7939/R3635N

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Design, synthesis, and screening of a library of peptidyl bis-boroxoles as low molecular weight receptors for complex oligosaccharides in neutral water: identification of a selective receptor for the tumour marker TF-antigen Open Access

Descriptions

Other title
Subject/Keyword
Oligosaccharides
Carbohydrates -- Synthesis
Organoboron compounds -- Synthesis
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Pal, Arnab
Supervisor and department
Dr. Dennis G. Hall (Department of Chemistry)
Examining committee member and department
Dr. Mario F. Feldman (Department of Biological Sciences)
Dr. Todd L. Lowary (Department of Chemistry)
Department
Department of Chemistry
Specialization

Date accepted
2009-10-13T21:39:02Z
Graduation date
2009-11
Degree
Master of Science
Degree level
Master's
Abstract
The ability of boronic acids to bind reversibly to simple carbohydrates in neutral water can be exploited to address the problem of cell-surface recognition. Recently, it has been shown that benzoboroxole can complex hexopyranosides under physiological conditions. These hemiboronate units were essential to the design of a small library of welldefined peptidyl-diboroxole receptors for complex oligosaccharides. The library was synthesized using a combinatorial solid-phase approach with the Irori® technology, and it was screened in a biochemical assay for the selective recognition of the T-antigen disaccharide, a cancer-associated cell-surface marker. A few high-affinity receptors of low micromolar IC50 were identified, and their binding behavior in neutral water was characterized using competition experiments and a systematic evaluation of analogues. These results suggest that low molecular weight receptors for biologically relevant glycoconjugates could be made to rival the efficiency of Nature’s carbohydratebinding proteins.
Language
English
DOI
doi:10.7939/R3635N
Rights
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 these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before 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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