Enolization and Oxidation Reactions of Reducing Sugars
1973; American Chemical Society; Linguagem: Inglês
10.1021/ba-1971-0117.ch005
ISSN0065-2393
Autores Tópico(s)Diet, Metabolism, and Disease
ResumoRecent progress is reported in investigations of enolization and ketonization of reducing sugars, oxidation of sugars with oxygen, and oxidation of sugars with sodium peroxide. The enolate mechanism for isomerization of aldoses and ketoses was confirmed by production of tritium-free fructose from D-glucose-2-t. The proportions of D-glucose, D-fructose, and D-mannose obtained by alkaline rearrangements of these sugars suggest that rearrangements of the three sugars occur through slightly different enolic intermediates. Mechanisms are suggested for degradation of the sugar to D-arabinonic and formic acids with and without hydride transfer. Alkaline peroxides are shown to convert aldoses almost quantitatively into formic acid. Ketoses yield formic and glycolic acids, and 6-deoxy-aldoses yield formic and acetic acids. Mechanisms are presented for oxidative degradation of α-hydroxy carbonyl compounds by alkaline hydroperoxide.
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