title: Synthesis of Nucleoside Triphosphates from 2'-3'-Protected Nucleosides Using Trimetaphosphate.
abstract: Chemists have been attempting to triphosphorylate nucleosides and other alcohols using trimetaphosphate (TriMP) since the 1960s. However, this route appears to have been abandoned due to poor yields. The first practical syntheses of nucleoside triphosphates (NTPs) are reported using TriMP as the key reagent. This was achieved by reacting the tetrabutylammonium salt of TriMP with mesitylenesulfonyl chloride in the presence of DABCO in pyridine followed by the addition of an appropriately protected nucleoside and phthalimide. Quenching the reaction with aqueous buffer followed by hydrolysis of the OH protecting groups gave the NTPs in good yield.
authors.affiliation: Faculty of Pharmacy, The British University in Egypt , Cairo-Suez Desert Road, 11837 Cairo, Egypt.
authors.forename: Samy
authors.initials: S
authors.lastname: Mohamady
authors.affiliation: Department of Chemistry, University of Waterloo , 200 University Avenue West, Waterloo, Ontario, Canada N2L 3G1.
authors.forename: Scott D
authors.initials: SD
authors.lastname: Taylor
mesh_terms: D006868:Hydrolysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry*; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D010755:Organophosphates / Q000737:chemistry*; D011725:Pyridines
chemical_list: D007202:Indicators and Reagents; D009705:Nucleosides; D009711:Nucleotides; D010755:Organophosphates; D011725:Pyridines; C023666:pyridine