Characterization of D-glucaric acid using NMR, X-ray crystal structure, and MM3 molecular modeling analyses.
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.
Shafizadeh Rocky Mountain Center for Wood and Carbohydrate Chemistry, The University of Montana, Missoula, MT 59812, USA. travis.denton@mail.ewu.edu
Travis T
TT
Denton
Kenneth I
KI
Hardcastle
Michael K
MK
Dowd
Donald E
DE
Kiely
D002236:Carbohydrate Conformation; D002247:Carbon Isotopes / Q000737:chemistry; D018360:Crystallography, X-Ray; D003903:Deuterium / Q000737:chemistry; D005937:Glucaric Acid / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009010:Monte Carlo Method
D002247:Carbon Isotopes; D003903:Deuterium; D005937:Glucaric Acid