title: Ethynyl, 2-Propynyl, and 3-Butynyl C-Phosphonate Analogues of Nucleoside Di- and Triphosphates: Synthesis and Reactivity in CuAAC.
abstract: The synthesis and reactivity of a novel class of clickable nucleotide analogues containing a C-phosphonate subunit that has an alkyne group at the terminal position of the oligophosphate chain are reported. The C-phosphonate subunits were prepared by simple one- or two-step procedures using commercially available reagents. Nucleotides were prepared by MgCl2-catalyzed coupling reactions and then subjected to CuAAC reactions with various azide compounds to afford 5'-γ-labeled nucleoside triphosphates in excellent yields.
authors.affiliation: †Division of Biophysics, Institute of Experimental Physics, Faculty of Physics, University of Warsaw, Zwirki i Wigury 93, 02-089 Warsaw, Poland.
authors.forename: Przemyslaw
authors.initials: P
authors.lastname: Wanat
authors.affiliation: ‡Centre of New Technologies, University of Warsaw, Banacha 2c, 02-097 Warsaw, Poland.|§College of Inter-Faculty Individual Studies in Mathematics and Natural Sciences, University of Warsaw, Zwirki i Wigury 93, 02-089 Warsaw, Poland.
authors.forename: Sylwia
authors.initials: S
authors.lastname: Walczak
authors.affiliation: ‡Centre of New Technologies, University of Warsaw, Banacha 2c, 02-097 Warsaw, Poland.
authors.forename: Blazej A
authors.initials: BA
authors.lastname: Wojtczak
authors.affiliation: †Division of Biophysics, Institute of Experimental Physics, Faculty of Physics, University of Warsaw, Zwirki i Wigury 93, 02-089 Warsaw, Poland.|∥Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093, Warsaw, Poland.
authors.forename: Monika
authors.initials: M
authors.lastname: Nowakowska
authors.affiliation: ‡Centre of New Technologies, University of Warsaw, Banacha 2c, 02-097 Warsaw, Poland.
authors.forename: Jacek
authors.initials: J
authors.lastname: Jemielity
authors.affiliation: †Division of Biophysics, Institute of Experimental Physics, Faculty of Physics, University of Warsaw, Zwirki i Wigury 93, 02-089 Warsaw, Poland.
authors.forename: Joanna
authors.initials: J
authors.lastname: Kowalska
mesh_terms: D001386:Azides / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D063065:Organophosphonates / Q000737:chemistry*; D011122:Polyphosphates / Q000737:chemistry*
chemical_list: D001386:Azides; D009705:Nucleosides; D009711:Nucleotides; D063065:Organophosphonates; D011122:Polyphosphates; C005692:triphosphoric acid