title: Nucleotides and nucleic acids: a source of inspiration for the development of new, phosphorus-centered functional groups.
abstract: Synthetic methodologies aiming at the creation of new phosphorus-centered functional groups are reported, as well as applications to the field of nucleotide chemistry. Thus, difluorophosphonothioate-based, ionic reagents 3b and 3d are shown to allow the stereocontrolled and efficient synthesis of phosphonodifluoromethyl analogues of nucleoside-3'-phosphates. An alternate, radical approach describes the use of hypophosphorous acid to stereoselectively link two furanosyl units in positions 3 and 5, and to provide an access to alpha,alpha-difluoro-H-phosphinates. These intermediates are shown to be precursors to the corresponding fluorinated phosphonic acids, phosphonothioic acids and variously substituted phosphinates.
authors.affiliation: University of Rouen, Laboratoire des Fonctions Azotées et Oxygénées Complexes, UMR 6014 CNRS, IRCOF, rue Tesnières, Mont Saint Aignan, France.
authors.forename: Chrystel
authors.initials: C
authors.lastname: Lopin
authors.forename: Goulnara
authors.initials: G
authors.lastname: Garipova
authors.forename: Irina
authors.initials: I
authors.lastname: Kalinina
authors.forename: Pierre
authors.initials: P
authors.lastname: Raboisson
authors.forename: Tomohisa
authors.initials: T
authors.lastname: Osaki
authors.forename: Arnaud
authors.initials: A
authors.lastname: Gautier
authors.forename: Sébastien
authors.initials: S
authors.lastname: Balieu
authors.forename: Carmen
authors.initials: C
authors.lastname: Salcedo
authors.forename: Géraldine
authors.initials: G
authors.lastname: Gouhier
authors.forename: Serge R
authors.initials: SR
authors.lastname: Piettre
mesh_terms: D009696:Nucleic Acids / Q000737:chemistry*; D009711:Nucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D010755:Organophosphates / Q000737:chemistry*; D010721:Phosphinic Acids / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D009696:Nucleic Acids; D009711:Nucleotides; D010755:Organophosphates; D010721:Phosphinic Acids