Comparison of the reducing power of aldose solutions

Concentration and temperature dependences of the redox potentials of neutral and alkaline solutions of glucose, mannose, galactose, galacturonic acid, and xylose were measured. Axial orientation of the secondary hydroxy groups in epimeric hexopyranoses, oxidation of C 6 to carboxy group, and the lack of primary hydroxy group in going to aldopentopyranose favor increasing (in the order of listing) destabilization of their cyclic structure, formation of the oxo form, and thermally activated retro-aldol reaction of the latter in alkaline medium. This leads to enhancement of their reducing power and chemical reactivity toward 5,5′,7,7′-tetrabromoindigo.