Characterization of D-glucaric acid using NMR, X-ray crystal structure, and MM3 molecular modeling analyses.

Travis T Denton, Kenneth I Hardcastle, Michael K Dowd, Donald E Kiely

Shafizadeh Rocky Mountain Center for Wood and Carbohydrate Chemistry, The University of Montana, Missoula, MT 59812, USA. travis.denton@mail.ewu.edu

Carbohydrate research 2011 Nov 29

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D-Glucaric acid was characterized in solution by comparing NMR spectra from the isotopically unlabeled molecule with those from D-glucaric acid labeled with deuterium or carbon-13 atoms. The NMR studies provided unequivocal assignments for all carbon atoms and non-hydroxyl protons of the molecule. The crystal structure of D-glucaric acid was obtained by X-ray diffraction techniques and the structure was a close match to the low energy conformation generated from a Monte-Carlo-based searching protocol employing the MM3 molecular mechanics program. The molecule adopts a bent structure in both the crystalline and computationally generated lowest-energy structure, a conformation that is devoid of destabilizing eclipsed 1,3-hydroxyl interactions. Copyright © 2011 Elsevier Ltd. All rights reserved.

Citation

Travis T Denton, Kenneth I Hardcastle, Michael K Dowd, Donald E Kiely. Characterization of D-glucaric acid using NMR, X-ray crystal structure, and MM3 molecular modeling analyses. Carbohydrate research. 2011 Nov 29;346(16):2551-7