Phosphorylation of D-glucose derivatives with inorganic monoimido-cyclo-triphosphate.
Phosphorylation of several D-glucose derivatives has been achieved using inorganic monoimido-cyclo-triphosphate (MCTP, Na(3)P(3)O(8)NH) in aqueous solution. In the phosphorylation of D-glucose, D-glucuronic acid, 2-deoxy-D-glucose and D-galactose, 1-O-diphosphoramidophosphono-beta-D-glucose, 1-O-diphosphoramidophosphono-beta-D-glucuronic acid, 1-O-diphosphoramidophosphono-2-deoxy-beta-D-glucose, and 1-O-diphosphoramidophosphono-beta-D-galactose were stereoselectively synthesized with yields of 54, 32, 37 and 46%, respectively. In the case of methyl alpha-D-glucoside, the phosphorylated products were methyl 3-O-diphosphoramidophosphono-alpha-D-glucoside and methyl 4-O-diphosphoramidophosphono-alpha-D-glucoside, and in the case of methyl beta-D-glucoside the products were methyl 2-O-diphosphoramidophosphono-beta-D-glucoside, methyl 3-O-diphosphoramidophosphono-beta-D-glucoside, and methyl 4-O-diphosphoramidophosphono-beta-D-glucoside. For D-mannose and D-allose, several phosphorylated products were obtained and the main products were 1-O-diphosphoramidophosphono-beta-D-aldoses.
Inoue
Hideko
H
Department of Functional Molecular Chemistry, Kobe Pharmaceutical University, Kobe, Japan.
Yamada
Tomoyuki
T
Nakayama
Hirokazu
H
Tsuhako
Mitsutomo
M
D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D015394:Molecular Structure; D010766:Phosphorylation; D011122:Polyphosphates / Q000737:chemistry*; D012015:Reference Standards; D012680:Sensitivity and Specificity; D013997:Time Factors
D007094:Imides; D011122:Polyphosphates; C516188:monoimido-cyclo-triphosphate; D005947:Glucose