(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → D-Glucosone

Participants

Reaction Conditions

Reaction Steps

Thin layer chromatography (TLC). Avicel coated glass plates are developed with an 8:8:2:4 (by volume); isopropanol:pyridine:acetic acid:water solvent system. Glucose and fructose have Rf 's 0.5-0.6; D-glucosone has an Rf 0.4-0.5 streak. (Rf =the distance substance migrates from origin/solvent front distance from origin). When the plates are sprayed with triphenyltetrazolium chloride (2% TTC in 0.5 N NaOH), both D-glucosone and fructose instantly yield red spots; glucose yields a red spot only upon heating for ten minutes at 100° C. When the plates are sprayed with diphenylamine/aniline/phosphoric acid/ethyl acetate reagent, (0.15 g/0.8 ml/11 ml/100ml), glucose yields a brown spot; D-glucosone yields a purple streak; and fructose yields a yellow spot upon heating for 10 minutes at 95° C.

Provenance & Evidence