AN INVESTIGATION OF THE RELATIONSHIP BETWEEN SWEETNESS AND INTRAMOLECULAR HYDROGEN-BONDING NETWORKS IN HEXULOSES USING THE SEMIEMPIRICAL MOLECULAR-ORBITAL METHOD, AM1

The AMI optimized geometries and energies of the pyranoid forms of two naturally occurring sugars, D-fructose and L-sorbose, and of the synthetic derivatives, 5-deoxy-D-threo-hexulose (5-deoxyfructose) and the carbocyclic analogue of D-fructose (pseudo-D-fructose), provide an explanation for the relative sweetness of these compounds. A novel approach to predicting the global energy minima of monosaccharides is presented. © 1990, American Chemical Society. All rights reserved.