Me. Brewster et al., AN AM1 MOLECULAR-ORBITAL STUDY OF ALPHA-D-GLUCOPYRANOSE AND BETA-MALTOSE - EVALUATION AND IMPLICATIONS, Carbohydrate research, 242, 1993, pp. 53-67
Chemical reactivity and other characteristics of alpha-D-glucopyranose
and beta-maltose were evaluated within a semiempirical molecular orbi
tal (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 (O
H-6), which is consistent with experimental findings. In addition, the
enhanced reactivity of the OH-3 locus, which is observed upon OH-2 al
kylation of the object sugars, was rationalized in terms of increased
OH-3 acidity. The chemical behavior of the monomers examined may be in
sightful in explaining the reactivity of glucopyranose polymers.