title: Phosphorylation of disaccharides with inorganic cyclo-triphosphate in aqueous solution.
abstract: 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.
authors.affiliation: Department of Functional Molecular Chemistry, Kobe Pharmaceutical University, Japan.
authors.forename: Hideko
authors.initials: H
authors.lastname: Inoue
authors.forename: Naoto
authors.initials: N
authors.lastname: Tone
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Nakayama
authors.forename: Mitsutomo
authors.initials: M
authors.lastname: Tsuhako
mesh_terms: 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
chemical_list: D004187:Disaccharides; D010755:Organophosphates; D010710:Phosphates; D012996:Solutions; C414399:cyclotriphosphoric acid; D014867:Water