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Title: Characterization of D-glucaric acid using NMR, x-ray crystal structure, and MM3 molecular modeling analyses

Author
item DENTON, TRAVIS - Washington University
item HARDCASTLE, KENNETH - Emory University
item Dowd, Michael
item KIELY, DONALD - University Of Montana

Submitted to: Carbohydrate Research
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 8/17/2011
Publication Date: 8/31/2011
Citation: Denton, T.T., Hardcastle, K.I., Dowd, M.K., Kiely, D.E. 2011. Characterization of D-glucaric acid using NMR, x-ray crystal structure, and MM3 molecular modeling analyses. Carbohydrate Research. 346:2551-2557.

Interpretive Summary: The structure of D-glucaric acid, a diacid derivative of glucose that is useful for generating amide-based polymers, was studied by NMR spectroscopy, X-ray crystallography, and computation chemistry methods. In general, the methods produced a picture of a molecule that prefers a “bent” conformation that does not have potentially 1,3 oxygen-oxygen interactions. The X-ray and lowest-energy modeling structures were in good agreement but with NMR data in solution yielded a somewhat different “average” conformation. The data should be of interest to researchers working to understand the properties of polymeric materials formed from D-glucaric acid.

Technical Abstract: 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.