Phosphorylation of disaccharides with inorganic cyclo-triphosphate in aqueous solution.
The phosphorylation of disaccharides by inorganic cyclo-triphosphate (P(3m)) with a six-membered ring was examined in aqueous solution. In the phosphorylation of cellobiose, lactose, and alpha,alpha-trehalose with P(3m), beta-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl 1-triphosphate, beta-D-galactopyranosyl-(1-->4)-beta-D-glucopyranosyl 1-triphosphate, and 3-O-triphospho-alpha-D-glucopyranosyl-(1-->1)-alpha-D-glucopyranoside were synthesized with maximum yields of 28%, 35%, and 20%, respectively. In the reactions of maltose and sucrose with P(3m), two phosphorylated products were obtained in yields of 42% and 58%, respectively. The main phosphorylated products were assigned to alpha-D-glucopyranosyl-(1-->4)-beta-D-glucopyranosyl 1-triphosphate and beta-D-fructofuranosyl-(2-->1)-2-O-triphospho-alpha-D-glucopyranoside by heteronuclear multiple bond correlation (HMBC) NMR. The phosphorylation mechanism of disaccharides with P(3m) is discussed.
Inoue
Hideko
H
Department of Functional Molecular Chemistry, Kobe Pharmaceutical University, Japan.
Tone
Naoto
N
Nakayama
Hirokazu
H
Tsuhako
Mitsutomo
M
D004187:Disaccharides / Q000737:chemistry / Q000378:metabolism*; D010755:Organophosphates / Q000737:chemistry / Q000378:metabolism*; D010710:Phosphates / Q000737:chemistry / Q000378:metabolism*; D010766:Phosphorylation; D012996:Solutions; D014867:Water / Q000737:chemistry
D004187:Disaccharides; D010755:Organophosphates; D010710:Phosphates; D012996:Solutions; C414399:cyclotriphosphoric acid; D014867:Water