Pyranose to Furanose Interconversion as a Function of Time and Water

1 Pyranose to Furanose Interconversion as a Function of Time and Water 

A re-examination of this work was conducted by Norrild and Eggert. Employing C-1 and C-6 labelled D-glucose the Jci-ci and /cs-c6 coupling constants were monitored. Exploiting the observed reduction in the /cc 

Drawing these observations together we indicate that the apparent dependence of the stability constants (A ) of monoboronic acids on the ability of the vicinal diols of saccharides to conform to a 5y -periplanar arrangement could be used to explain the heightened stability of D-fructose over other monosaccharides, see Lorand and Edwards results in Table 1. 

From a simplistic viewpoint, we indicated that a very general statistical trend appears to exist between the natural speciation of saccharide forms containing the xy -periplanar anomeric hydroxyl pair arrangement (a premise of the form s stability) and the qualitative trend observed for their stability constants K) with monoboronic acids. Table 2. 

Unfortunately, the complexity and extensive number of possible binding motifs precludes such a simplistic approach from providing anything other than a statistical rule-of-thumb guide. 

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