Structure of D-Fructosamine Hydrochloride and D-Fructosamine Hydroacetate

D-Fructosamine derivatives are key intermediates of the early Maillard reaction and have been a subject of numerous studies in food and health sciences due to their implication in the nutritional and organoleptic quality of foods, as well as to complications in diabetes and renal disease. We report...

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Bibliographic Details
Published inJournal of carbohydrate chemistry Vol. 28; no. 5; pp. 245 - 263
Main Authors Mossine, Valeri V., Barnes, Charles L., Mawhinney, Thomas P.
Format Journal Article
LanguageEnglish
Published Taylor & Francis Group 06.07.2009
Subjects
1-Amino-1-deoxy-D-fructose
Amadori compound
Crystal structure
D-Fructosamine
NMR
β-D-Fructopyranose
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Summary:D-Fructosamine derivatives are key intermediates of the early Maillard reaction and have been a subject of numerous studies in food and health sciences due to their implication in the nutritional and organoleptic quality of foods, as well as to complications in diabetes and renal disease. We report the crystal structure analyses of 1-deoxy-β -D-fructopyranos-1-ylamine hydrochloride (1) and -hydroacetate (2) salts. The carbohydrate rings adopt the normal 2 C 5 pyranose chair conformation in 1 and 2. Bond lengths and valence angles in 1 and 2 compare well with the average values from related pyranose structures. There are two conformationally nonequivalent molecules in the asymmetric unit in 1. All hydroxyl and ring oxygen atoms, ammonium groups, and chloride ions in 1 are involved in an extensive three-dimensional hydrogen bonding network. The hydrogen bonding network in 2 is formed by one type of infinite chain with attached antidromic cycles.
ISSN:0732-8303
1532-2327
DOI:10.1080/07328300902974769