Molecular modeling of poly(ethylene oxide) model cofactors; 1,3,6-tri-O-galloyl-beta- d-glucose and corilagin

Roger Gaudreault; Theo G M van de ven; Michael A Whitehead

doi:10.1007/s00894-001-0070-9

Molecular modeling of poly(ethylene oxide) model cofactors; 1,3,6-tri-O-galloyl-beta- d-glucose and corilagin

J Mol Model. 2002 Mar;8(3):73-80. doi: 10.1007/s00894-001-0070-9.

Authors

Roger Gaudreault¹, Theo G M van de ven, Michael A Whitehead

Affiliation

¹ Department of Chemistry, McGill University, 801, Sherbrooke St. W, Montreal, Qc, Canada.

PMID: 12111394
DOI: 10.1007/s00894-001-0070-9

Abstract

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.

MeSH terms

Carbohydrate Conformation
Gallic Acid / analogs & derivatives
Gallic Acid / chemistry*
Glucose / analogs & derivatives
Glucose / chemistry*
Glucosides / chemistry*
Hydrolyzable Tannins
Models, Molecular*
Molecular Structure
Phenols / chemistry
Polyethylene Glycols / chemistry
Rotation
Spectrophotometry, Infrared

Substances

Glucosides
Hydrolyzable Tannins
Phenols
Polyethylene Glycols
corilagin
Gallic Acid
Glucose
1,3,6-tri-O-galloylglucose