This work was partly supported by the University of Missouri Agriculture Experiment Station Laboratories. We wish to thank Dr. Wei G. Wycoff and Dr. Shaokai Jiang for help with the NMR experiments.
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Communication
Stabilization of the Acyclic Tautomer in Reducing Carbohydrates†
Article first published online: 23 JUN 2009
DOI: 10.1002/anie.200902123
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Mossine, V., Barnes, C., Chance, D. and Mawhinney, T. (2009), Stabilization of the Acyclic Tautomer in Reducing Carbohydrates. Angewandte Chemie International Edition, 48: 5517–5520. doi: 10.1002/anie.200902123
- †
Publication History
- Issue published online: 8 JUL 2009
- Article first published online: 23 JUN 2009
- Manuscript Received: 20 APR 2009
Funded by
- University of Missouri Agriculture Experiment Station Laboratories
Keywords:
- carbohydrates;
- hydrophobic effect;
- solid-state structures;
- tautomerism
Graphical Abstract
Sweet structure: Acyclic reducing carbohydrate intermediates are typically impossible to crystallize. 1-Amino-1-deoxy-D-fructose derivatives afford an exceptional example of the keto form in the crystalline state (see structure), possibly as a consequence of an interplay between the hydrophobic microenvironment around the carbonyl group and hydrogen-bonding patterns.