The hydrolysis of α-and β-hexopyranosyl phosphates

The hydrolysis of the anomeric pairs of the aldopyranosyl phosphates of d-glucose, d-mannose, d-galactose, and l-fucose was studied over the pH range of 1-6. The hydrolysis of the acidic “neutral” species is strongly influenced by the structure of the pyranosyl group. The presence of axial hydroxyl...

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Bibliographic Details
Published in:Carbohydrate research 1979, Vol.73 (1), p.227-234
Main Authors: O'Connor, John V., Barker, Robert
Format: Article
Language:English
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Summary:The hydrolysis of the anomeric pairs of the aldopyranosyl phosphates of d-glucose, d-mannose, d-galactose, and l-fucose was studied over the pH range of 1-6. The hydrolysis of the acidic “neutral” species is strongly influenced by the structure of the pyranosyl group. The presence of axial hydroxyl groups, or of the electron donating methyl group on C-5 (as in l-fucose), greatly enhances the rate of hydrolysis relative to that of d-glucopyranosyl phosphate. In contrast, the hydrolysis of the monoanionic species is mainly influenced by the anomeric configuration, the β anomers of the pyranosyl phosphates being hydrolysed 3-7 times as fast as the α anomers.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(00)85492-0