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Mathematical analysis of the mutarotation of sugars

1975; Elsevier BV; Volume: 40; Issue: 2 Linguagem: Inglês

10.1016/s0008-6215(00)82606-3

1873-426X

Hiromasa Kijima, Nobuhiro Gō,

DNA and Nucleic Acid Chemistry

Abstract The tautomerism of sugars showing complex mutarotation has been analyzed mathematically based on a scheme of three components. More-complete but complex schemes are shown to be reducible to the three-component scheme, because the supposed intermediates of interconversion can be neglected in the kinetics when their equilibrium contents are very small and because two furanose tautomers can be regarded as one component under appropriate conditions. The kinetics of the three-component scheme have been fully studied and are shown to explain successfully the tautomerism of most of the sugars. The tautomerism of D -galactose has been analyzed in especial detail. From the polarimetric data and the equilibrium content of α-pyranose, the kinetic rate-constants for D -galactose were determined and found consistent with all other experimental data. The slow and fast processes of complex mutarotation of D -galactose are shown to correspond approximately to pyranose-pyranose and pyranose-furanose interconversions, respectively.