title: NMR studies of the conformation of the natural sweetener rebaudioside A.
abstract: Rebaudioside A is a natural sweetener from Stevia rebaudiana in which four beta-D-glucopyranose units are attached to the aglycone steviol. Its (1)H and (13)C NMR spectra in pyridine-d(5) were assigned using 1D and 2D methods. Constrained molecular dynamics of solvated rebaudioside using NMR constraints derived from ROESY cross peaks yielded the orientation of the beta-D-glucopyranose units. Hydrogen bonding was examined using the temperature coefficients of the hydroxyl chemical shifts, ROESY and long-range COSY spectra, and proton-proton coupling constants.
authors.affiliation: Chemistry Department, Pomona College, Claremont, CA 91711, United States. wsteinmetz@pomona.edu
authors.forename: Wayne E
authors.initials: WE
authors.lastname: Steinmetz
authors.forename: Alvin
authors.initials: A
authors.lastname: Lin
mesh_terms: D002236:Carbohydrate Conformation; D045786:Diterpenes, Kaurane / Q000737:chemistry*; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D056004:Molecular Dynamics Simulation; D012996:Solutions; D013549:Sweetening Agents
chemical_list: D045786:Diterpenes, Kaurane; D012996:Solutions; D013549:Sweetening Agents; C025474:rebaudioside A