title: A P(V)-N activation strategy for the synthesis of nucleoside polyphosphates.
abstract: A general and high-yielding synthesis of nucleoside 5'-triphosphates (NTPs) and nucleoside 5'-diphosphates (NDPs) from protected nucleoside 5'-phosphoropiperidates promoted by 4,5-dicyanoimidazole (DCI) has been developed. (31)P NMR tracing experiments showed that the sequential deprotection and coupling reactions were exceptionally clean. The phosphoropiperidate exhibited superior reactivity to the conventional phosphoromorpholidate toward DCI-promoted NTP/NDP synthesis. The experimental results suggested that the mechanism of DCI activation could be distinctive for NTP and NDP synthesis, depending on the different nucleophilicity of pyrophosphate and phosphate.
authors.affiliation: Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, 605 Fenglin Avenue, Nanchang, Jiangxi 330013, P. R. China. sunqi96@tsinghua.org.cn
authors.forename: Qi
authors.initials: Q
authors.lastname: Sun
authors.forename: Shanshan
authors.initials: S
authors.lastname: Gong
authors.forename: Jian
authors.initials: J
authors.lastname: Sun
authors.forename: Si
authors.initials: S
authors.lastname: Liu
authors.forename: Qiang
authors.initials: Q
authors.lastname: Xiao
authors.forename: Shouzhi
authors.initials: S
authors.lastname: Pu
mesh_terms: D000577:Amides / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D010756:Phosphoric Acids / Q000737:chemistry*; D011122:Polyphosphates / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C110830:4,5-dicyanoimidazole; D000577:Amides; D007093:Imidazoles; D009705:Nucleosides; D010756:Phosphoric Acids; D011122:Polyphosphates; C011067:phosphoramidic acid