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.
Department of Chemistry, McGill University, 801, Sherbrooke St. W, Montreal, Qc, Canada.
Roger
R
Gaudreault
Theo G M
TG
van de ven
Michael A
MA
Whitehead
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