An AM1 molecular orbital study of alpha-D-glucopyranose and beta-maltose: evaluation and implications.
Chemical reactivity and other characteristics of alpha-D-glucopyranose and beta-maltose were evaluated within a semiempirical molecular orbital (AM1) framework. Theoretically generated structures compared well to those determined by X-ray crystallographic techniques. Calculations suggested that the secondary hydroxy functions (OH-2 and OH-3) of the mono- and di-saccharides were more acidic than the primary alcohol (OH-6), which is consistent with experimental findings. In addition, the enhanced reactivity of the OH-3 locus, which is observed upon OH-2 alkylation of the object sugars, was rationalized in terms of increased OH-3 acidity. The chemical behavior of the monomers examined may be insightful in explaining the reactivity of glucopyranose polymers.
Brewster
M E
ME
Center for Drug Discovery, College of Pharmacy, University of Florida, Gainesville 32610.
Huang
M J
MJ
Pop
E
E
Pitha
J
J
Dewar
M J
MJ
Kaminski
J J
JJ
Bodor
N
N
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005947:Glucose / Q000737:chemistry*; D008320:Maltose / Q000737:chemistry*; D008958:Models, Molecular; D008969:Molecular Sequence Data; D013816:Thermodynamics; D014961:X-Ray Diffraction
D008320:Maltose; D005947:Glucose