A kinetic analysis of the reactivities of the hydroxyl groups in formylation of the D-glucopyranosyl residues in dextrin

The kinetics of the homogeneous formylation of dextrin with 90% formic acid have been analyzed as the composite of four, simultaneous, independent, reversible reactions at the C-2, C-3, and C-6 hydroxyl groups of each D-glucopyranosyl residue and the C-4 hydroxyl group on the terminal D-glucopyranos...

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Bibliographic Details
Published in:Carbohydrate research 1967, Vol.3 (3), p.361-368
Main Authors: Rowland, Stanley P., Brannan, Mary Ann F., Janssen, Hermann J., Pittman, Paul F.
Format: Article
Language:English
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Summary:The kinetics of the homogeneous formylation of dextrin with 90% formic acid have been analyzed as the composite of four, simultaneous, independent, reversible reactions at the C-2, C-3, and C-6 hydroxyl groups of each D-glucopyranosyl residue and the C-4 hydroxyl group on the terminal D-glucopyranosyl group of each molecule. The velocity coefficient and the equilibrium constant for the primary hydroxyl group are higher than the values for the (secondary) C-2 and C-3 hydroxyl groups. Results of the kinetic analysis suggest that one secondary hydroxyl group is esterified rapidly to a low level of equilibrium, whereas the other secondary hydroxyl group is slowly esterified to a higher level of equilibrium. These results are shown to be qualitatively consistent with the behavior of other carbohydrates on esterification or de-esterification.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(00)82212-0