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United States Department of Agriculture

Agricultural Research Service

Title: Functionalized Beta-C-Glycosidic Ketone Hydrazones: Novel Derivatives for Carbohydrate Analysis by Maldi-Tof Mass Spectrometry

Authors
item Price, Neil
item Sheng, Suzie

Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: October 1, 2005
Publication Date: October 1, 2005
Citation: Price, N.P., Sheng, S.S. 2005. Functionalized beta-c-glycosidic ketone hydrazones: novel derivatives for carbohydrate analysis by MALDI-TOF mass spectrometry [abstract]. Midwest Carbohydrate. p. 4.

Technical Abstract: Hydrazones constitute one of the best derivatives for the analysis of aldehydes and ketones yielding crystalline solids that are readily precipitated from water. 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. The first equivalent forms an imine with the aldehyde or ketone group. The second equivalent oxidizes the alcohol adjacent to the first imine to a carbonyl group. The newly formed carbonyl then reacts with a third equivalent of the hydrazone to give an osazone. Since the reaction is at C1 and C2, a ketose will therefore give the same osazone as the related aldose. For the same reason C2-epimers, such as glucose and mannose, also give rise to identical osazones. This well known reaction has therefore tended to limit the useful of hydrazones for the analysis of sugars. Here we show the potential of new carbohydrate-based derivatives, beta-C-glycosidic ketones, for the formation of various functionalized hydrazones.

Last Modified: 10/26/2014