Base catalysed isomerisation of aldoses of the arabino and lyxo series in the presence of aluminate

Carbohydr Res. 2002 Apr 30;337(9):779-86. doi: 10.1016/s0008-6215(02)00065-4.

Abstract

Base-catalysed isomerisation of aldoses of the arabino and lyxo series in aluminate solution has been investigated. L-Arabinose and D-galactose give L-erythro-2-pentulose (L-ribulose) and D-lyxo-2-hexulose (D-tagatose), respectively, in good yields, whereas lower reactivity is observed for 6-deoxy-D-galactose (D-fucose). From D-lyxose, D-mannose and 6-deoxy-L-mannose (L-rhamnose) are obtained mixtures of ketoses and C-2 epimeric aldoses. Small amounts of the 3-epimers of the ketoses were also formed. 6-Deoxy-L-arabino-2-hexulose (6-deoxy-L-fructose) and 6-deoxy-L-glucose (L-quinovose) were formed in low yields from 6-deoxy-L-mannose and isolated as their O-isopropylidene derivatives. Explanations of the differences in reactivity and course of the reaction have been suggested on the basis of steric effects.

MeSH terms

  • Aluminum Oxide / chemistry*
  • Carbohydrate Conformation
  • Catalysis
  • Glucose / analogs & derivatives
  • Hydrogen-Ion Concentration
  • Isomerism
  • Molecular Structure
  • Monosaccharides / chemistry*
  • Solutions / chemistry
  • Xylose / analogs & derivatives

Substances

  • Monosaccharides
  • Solutions
  • Xylose
  • Glucose
  • Aluminum Oxide