Structures of D-threo-2,5-hexodiulose 1-phosphate and D-threo-2,5-hexodiulose 1,6-bisphosphate (5-keto-D-fructose mono- and bis-phosphate) in solution by 13C-N.M.R. spectroscopy.
The mono- (2) and bis-phosphate (3) derivatives of D-threo-2,5-hexodiulose (1) (5-keto-D-fructose) were synthesized enzymically and purified by anion-exchange chromatography. The proportions, sizes of ring, and anomeric configurations were determined by F.t. 31P- and 13C-n.m.r. spectroscopy. Compound 2 was found to exist preponderantly (70-78%) in the beta-pyranose form with the remainder existing in the 2R,5R-furanose form. Compound 3 assumes two different furanose forms in solution, one (77-84%) being the 2R,5R-furanose form and the other the 2S,5R-furanose form.
L
L
Butera
S
S
Englard
J S
JS
Blanchard
G
G
Avigad
D002236:Carbohydrate Conformation; D005632:Fructose / Q000031:analogs & derivatives / Q000138:chemical synthesis; D005635:Fructosediphosphates / Q000138:chemical synthesis; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D012996:Solutions
D005635:Fructosediphosphates; D007202:Indicators and Reagents; D012996:Solutions; C049418:D-2,5-hexodiulose 1-phosphate; D005632:Fructose; C017451:D-5-ketofructose 1,6-biphosphate