Author
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Carpenter, Chrissie |
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Submitted to: Meeting Abstract
Publication Type: Abstract Only Publication Acceptance Date: 3/25/2010 Publication Date: 3/25/2010 Citation: Carpenter, C.A. 2010. Carbohydrate C-Glycoside Ketones: Introducing Ketone Chemistry into Locked-Ring Aldose Sugars [abstract]. American Chemical Society. Interpretive Summary: Technical Abstract: Chemical modification of aldose sugars at the anomeric position typically results in ring opening, and therefore the loss of structural integrity of the parent sugar molecule. This produces modified carbohydrates that differ markedly from the parent molecule. The research presented here focuses on development of new carbohydrate "locked-ring" C-glycosides and the subsequent formation of functionalized ketohydrazones and oximes. This chemistry is accomplished using an aqueous-based, one-pot strategy that involves first converting the sugar to a C-glycoside ketone, followed by conversion to hydrazones or oximes. Activation of the anomeric center and protecting group manipulations are not required and the chemistry is mild enough for a wide range of carbohydrates, producing a variety of functionalized C-glycosides that all retain the closed ring conformation of the parent sugars. Using standard hydrazine/oxime chemistry the C-glycoside ketones can be tagged with fluorescence, colored, cationic, alkyl, or biotin-labeled groups, or immobilized onto hydrazine-functionalized beads. |
