NMR studies of the conformation of the natural sweetener rebaudioside A.
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.
Steinmetz
Wayne E
WE
Chemistry Department, Pomona College, Claremont, CA 91711, United States. wsteinmetz@pomona.edu
Lin
Alvin
A
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
D045786:Diterpenes, Kaurane; D012996:Solutions; D013549:Sweetening Agents; C025474:rebaudioside A