title: Highly regioselective C-5 iodination of pyrimidine nucleotides and subsequent chemoselective Sonogashira coupling with propargylamine.
abstract: An efficient C-5 iodination of pyrimidine-5'-triphosphates and subsequent palladium-catalyzed Sonogashira coupling reaction with propargylamine is described. The iodination reaction is highly regioselective and the coupling reaction is highly chemoselective that furnishes exclusive 5-(3-aminopropargyl)-pyrimidine-5'-triphosphate in good yield with high purity (>99%).
authors.affiliation: a Thermo Fisher Scientific , Bioorganic Chemistry Division , Austin , TX , USA.
authors.forename: Anilkumar R
authors.initials: AR
authors.lastname: Kore
authors.forename: Annamalai
authors.initials: A
authors.lastname: Senthilvelan
authors.forename: Muthian
authors.initials: M
authors.lastname: Shanmugasundaram
mesh_terms: D004247:DNA / Q000737:chemistry; D015195:Drug Design; D007455:Iodine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry; D010710:Phosphates / Q000737:chemistry; D011437:Propylamines / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D011742:Pyrimidine Nucleotides / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry
chemical_list: D009711:Nucleotides; D010710:Phosphates; D011437:Propylamines; D011725:Pyridines; D011742:Pyrimidine Nucleotides; D011743:Pyrimidines; C009054:propargylamine; D010165:Palladium; D004247:DNA; D007455:Iodine; D010293:Pargyline
keywords: Regioselective; Sonogashira coupling; aminopropargyl nucleotides; chemoselective; non-radioactive probe