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Molecular mapping of the acid catalysed dehydration of fructose
Geoffrey R Akien1, Long Qi, István T Horváth
1Department of Biology and Chemistry, City University of Hong Kong, 83 Tat Chee Avenue, Kowloon, Hong Kong SAR.
Abstract:
Several intermediates and different reaction paths were identified for the acid catalysed conversion of fructose to 5-(hydroxymethyl)-2-furaldehyde (HMF) in different solvents. The structural information combined with results of isotopic-labelling experiments allowed the determination of the irreversibility of the three steps from the fructofuranosyl oxocarbenium ion to HMF as well as the analogous pyranose route.
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Dehydration synthesis (also called a condensation reaction) is the chemical process in which two molecules covalently link together to form a new molecule, along with the release of a water molecule. Many physiologically important compounds form by dehydration synthesis reactions, such as complex carbohydrates, proteins, DNA, and RNA.
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Sugar molecules are covalently linked together by dehydration synthesis. During the reaction, the hydroxyl (-OH) group from...