Regioselective phosphorylation of branched cyclodextrins with cyclo-mono-mu-imidotriphosphate.
The phosphorylation of the branched cyclodextrins, mono-6-O-(alpha-D-glucopyranosyl)cyclomaltohexaose, mono-6-O-(alpha-D-maltosyl)cyclomaltohexaose, mono-6-O-(alpha-D-glucopyranosyl)cyclomaltoheptaose, and mono-6-O-(alpha-D-maltosyl)cyclomaltoheptaose, in aqueous solution by sodium cyclo-mono-mu-imidotriphosphate (cMITP) was examined. In these reactions, only the 2-OH group of a single alpha-D-glucopyranosyl residue of the cyclodextrin ring was phosphorylated, in a maximum yield of 67%. A possible mechanism for the phosphorylation is discussed.
Inoue
Hideko
H
Department of Functional Molecular Chemistry, Kobe Pharmaceutical University, Kobe 658-8558, Japan. i-hideko@kobepharma-u.ac.jp
Kawashita
Toyohiro
T
Nakayama
Hirokazu
H
Tsuhako
Mitsutomo
M
D002236:Carbohydrate Conformation; D002851:Chromatography, High Pressure Liquid; D003505:Cyclodextrins / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010710:Phosphates / Q000737:chemistry*; D017553:Phosphorus Compounds / Q000737:chemistry*; D010766:Phosphorylation; D021241:Spectrometry, Mass, Electrospray Ionization
D003505:Cyclodextrins; D010710:Phosphates; D017553:Phosphorus Compounds; C505967:cyclo-mono-mu-imidotriphosphate