A one-step phosphorylation of D-aldohexoses and D-aldopentoses with inorganic cyclo-triphosphate.
The phosphorylation reaction by inorganic cyclo-triphosphate (P3m) having a six-membered ring was examined for D-aldohexoses and D-aldopentoses in aqueous solution. Similar to the process for D-glucose, D-galactose, D-xylose or D-allose were phosphorylated with P3m to give stereoselectively beta-D-galactopyranosyl 1-triphosphate, beta-D-xylopyranosyl 1-triphosphate or beta-D-allopyranosyl 1-triphosphate with maximum yields of 31.3, 32.5 or 32.1%, respectively. On the other hand, in the reaction of D-ribose, D-lyxose, D-mannose or D-arabinose with P3m, the yields of beta-D-ribopyranosyl 1-triphosphate, alpha-D-lyxopyranosyl 1-triphosphate, alpha-D-mannopyranosyl 1-triphosphate or alpha-D-arabinopyranosyl 1-triphosphate were 8.0, 16.5, 9.6 or 14.1%, respectively. The phosphorylation mechanism of D-aldopyranoses with P3m was also discussed.
Inoue
H
H
Department of Functional Molecular Chemistry, Kobe Pharmaceutical University, Japan.
Nakayama
H
H
Tsuhako
M
M
D002851:Chromatography, High Pressure Liquid; D006601:Hexoses / Q000378:metabolism*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D010429:Pentoses / Q000378:metabolism*; D010710:Phosphates / Q000378:metabolism; D010766:Phosphorylation; D013403:Sugar Phosphates / Q000138:chemical synthesis*
D006601:Hexoses; D010429:Pentoses; D010710:Phosphates; D013403:Sugar Phosphates