Journal article
Characterization of d-glucaric acid using NMR, X-ray crystal structure, and mm3 molecular modeling analyses
Carbohydrate research, Vol.346(16), pp.2551-2557
2011
Handle:
https://hdl.handle.net/2376/108679
PMID: 22015400
Abstract
[Display omitted]
► We employ NMR and X-ray diffraction techniques to characterize
d-glucaric acid in aqueous solution and in the crystalline state, respectively. ► Molecular modeling analyses are employed to evaluate the conformational distribution of
d-glucaric acid. ►
1H and
13C NMR assignments of
d-glucaric acid are supported by spectral assignments from deuterium and carbon 13 labeled
d-glucaric acid. ► Crystalline
d-glucaric acid has a sickle conformation. ► The lowest energy computationally generated conformation of
d-glucaric acid is a close match to its crystal structure.
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.
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Details
- Title
- Characterization of d-glucaric acid using NMR, X-ray crystal structure, and mm3 molecular modeling analyses
- Creators
- Travis T Denton - Shafizadeh Rocky Mountain Center for Wood and Carbohydrate Chemistry, The University of Montana, Missoula, MT 59812, USAKenneth I Hardcastle - Emory University Crystallography Laboratory, Department of Chemistry, Emory University, Atlanta, GA 30322, USAMichael K Dowd - USDA Southern Regional Research Center, 1100 Robert E. Lee Blvd., New Orleans, LA 70126, USADonald E Kiely - Shafizadeh Rocky Mountain Center for Wood and Carbohydrate Chemistry, The University of Montana, Missoula, MT 59812, USA
- Publication Details
- Carbohydrate research, Vol.346(16), pp.2551-2557
- Academic Unit
- Pharmaceutical Sciences, Department of
- Publisher
- Elsevier Ltd
- Identifiers
- 99900547165801842
- Language
- English
- Resource Type
- Journal article