Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: 6/22/2006
Publication Date: 6/22/2006
Citation: Price, N.P. 2006. Functionalized beta-c-glycosidic ketone hydrazones. Novel derivatives for immobilization and end-labeling of carbohydrates [abstract]. Federation of American Society for Experimental Biology. p. 44.
Technical Abstract: Hydrazones are excellent derivatives for the analysis of aldehydes and ketones and are often readily prepared in quantitative yield. Unlike simple aldehydes and ketones, sugars do not usually form simple hydrazones. They react with three equivalents of aryl- or acylhydrazines at both the C1 and C2 carbons to give sugar osazones. Initially, an imine forms at the anomeric carbon. The adjacent hydroxyl is then oxidized to a carbonyl group, which reacts with a third equivalent of the hydrazone to give an osazone. Because the reaction is at C1 and C2, a ketose gives the same osazone as the related aldose, and C2-epimers, such as Man and Glc, also give identical osazones. The derivatized residue is acyclic, and retains little of the structural characteristics of the original sugar. This poster describes new carbohydrate-based derivatives, beta-C-glycosidic ketones for the formation of various functionalized hydrazones (phenyl, dansyl, dabsyl, Girard’s P reagent). Mono- and oligosaccharides give high yields from aqueous-based, one-pot reactions, and the functionalized C-glycosides retain a closed ring conformation. These derivatives have potential for end-labeling and immobilization of carbohydrates.