Illuminating glycoconjugate interactions and glycosyltransferase substrates using photocrosslinking sugar analogs

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The cell surface is composed of a heterogeneous array of proteins and lipids, many of which are modified by carbohydrate structures. Glycoconjugates, which include both glycoproteins and glycolipids, play vital roles in cellular functions, mediating communication with the extracellular environment. A frequent modification to cell surface carbohydrates is the addition of a nine-carbon [alpha]-keto acid, sialic acid. Sialic acid-dependent interactions are often characterized by large equilibrium dissociation constants and rapid dissociation rates, precluding the use of traditional biological techniques for isolating these complexes. To investigate glycan-mediated interactions, I employed the use of metabolic oligosaccharide engineering to introduce a panel of diazirine-modified sialic acids onto the cell surface. I demonstrate that the sialic acid analogs covalently trap both glycoprotein- and glycolipid-mediated interactions, illustrating the utility of the photoactivatable sugars. These results are significant as they yield a new set of tools for studying ephemeral interactions that are otherwise inaccessible.


Type of resource text
Form electronic; electronic resource; remote
Extent 1 online resource.
Publication date 2010
Issuance monographic
Language English


Associated with Bond, Michelle Rueffer
Associated with Stanford University, Department of Chemistry
Primary advisor Kohler, Jennifer, 1972-
Primary advisor Kool, Eric T
Thesis advisor Kohler, Jennifer, 1972-
Thesis advisor Kool, Eric T
Thesis advisor Harbury, Pehr
Advisor Harbury, Pehr


Genre Theses

Bibliographic information

Statement of responsibility Michelle Rueffer Bond.
Note Submitted to the Department of Chemistry.
Thesis Thesis (Ph.D.)--Stanford University, 2010.
Location electronic resource

Access conditions

© 2010 by Michelle Rueffer Bond
This work is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported license (CC BY-NC).

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