Molecular modeling of poly(ethylene oxide) model cofactors; 1,3,6-tri-O-galloyl-beta- d-glucose and corilagin.
The most stable structures of two poly(ethylene oxide) (PEO) model cofactors, beta-1-O-galloyl-3,6-( R)-hexahydroxydiphenoyl- d-glucose (corilagin) and 1,3,6-tri-O-galloyl-beta- d-glucose (TGG), are calculated using molecular modeling and PM3 semiempirical molecular orbital theories. The theoretical PM3 structures agree with interpreted structures from experimental NMR; the glucopyranose ring of corilagin has a boat and TGG a chair conformation, for which the heats of formation, torsion angles, distances, van der Waals surface, and the infrared spectra are calculated.
Gaudreault
Roger
R
Department of Chemistry, McGill University, 801, Sherbrooke St. W, Montreal, Qc, Canada.
van de ven
Theo G M
TG
Whitehead
Michael A
MA
D002236:Carbohydrate Conformation; D005707:Gallic Acid / Q000031:analogs & derivatives / Q000737:chemistry*; D005947:Glucose / Q000031:analogs & derivatives / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry*; D047348:Hydrolyzable Tannins; D008958:Models, Molecular; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry; D011092:Polyethylene Glycols / Q000737:chemistry; D012399:Rotation; D013055:Spectrophotometry, Infrared
D005960:Glucosides; D047348:Hydrolyzable Tannins; D010636:Phenols; D011092:Polyethylene Glycols; C049096:corilagin; D005707:Gallic Acid; D005947:Glucose; C477272:1,3,6-tri-O-galloylglucose