无机单亚氨基环三磷酸对D-葡萄糖衍生物的磷酸化作用。
Phosphorylation of D-glucose derivatives with inorganic monoimido-cyclo-triphosphate.
作者信息
Inoue Hideko, Yamada Tomoyuki, Nakayama Hirokazu, Tsuhako Mitsutomo
机构信息
Department of Functional Molecular Chemistry, Kobe Pharmaceutical University, Kobe, Japan.
出版信息
Chem Pharm Bull (Tokyo). 2006 Oct;54(10):1397-402. doi: 10.1248/cpb.54.1397.
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.
在水溶液中，使用无机单亚氨基环三磷酸酯（MCTP，Na₃P₃O₈NH）实现了几种D - 葡萄糖衍生物的磷酸化反应。在D - 葡萄糖、D - 葡萄糖醛酸、2 - 脱氧 - D - 葡萄糖和D - 半乳糖的磷酸化反应中，立体选择性地合成了1 - O - 二磷酰胺基膦酰基 - β - D - 葡萄糖、1 - O - 二磷酰胺基膦酰基 - β - D - 葡萄糖醛酸、1 - O - 二磷酰胺基膦酰基 - 2 - 脱氧 - β - D - 葡萄糖和1 - O - 二磷酰胺基膦酰基 - β - D - 半乳糖，产率分别为54%、32%、37%和46%。对于α - D - 葡萄糖甲基苷，磷酸化产物是3 - O - 二磷酰胺基膦酰基 - α - D - 葡萄糖甲基苷和4 - O - 二磷酰胺基膦酰基 - α - D - 葡萄糖甲基苷；对于β - D - 葡萄糖甲基苷，产物是2 - O - 二磷酰胺基膦酰基 - β - D - 葡萄糖甲基苷、3 - O - 二磷酰胺基膦酰基 - β - D - 葡萄糖甲基苷和4 - O - 二磷酰胺基膦酰基 - β - D - 葡萄糖甲基苷。对于D - 甘露糖和D - 阿洛糖，得到了几种磷酸化产物，主要产物是1 - O - 二磷酰胺基膦酰基 - β - D - 醛糖。
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