title: Expanding the borononucleotide family: synthesis of borono-analogues of dCMP, dGMP and dAMP.
abstract: We previously reported the synthesis of a borononucleotide analogue of thymidine monophosphate and its association towards the formation of a new borono-linked dinucleotide. Here we describe the completion of the set of four 2'-deoxyborononucleotide analogues of natural nucleotide monophosphates, namely the previously unknown dCbn, dGbn and dAbn. These analogues were all prepared from the respective 5'-aldehydic nucleosides through a homologation/reduction sequence. The borononucleotides were subsequently obtained by either borylation (dCbn and dGbn) or cross-metathesis (CM) in the presence of the Hoveyda-Grubbs catalyst (dAbn). The reversible formation of the corresponding dinucleotides between these new analogues and uridine was studied by (1)H NMR, and semi-empirical calculations were carried out to provide bond length and electrostatic information that assess the structural similarities existing between these bioisosteres and their natural counterparts.
authors.affiliation: Institut des Biomolécules Max Mousseron, UMR 5247 CNRS-Université Montpellier 1, place Eugène Bataillon, 34095 Montpellier, France.
authors.forename: Anthony R
authors.initials: AR
authors.lastname: Martin
authors.forename: Kishor
authors.initials: K
authors.lastname: Mohanan
authors.forename: Delphine
authors.initials: D
authors.lastname: Luvino
authors.forename: Nicolas
authors.initials: N
authors.lastname: Floquet
authors.forename: Carine
authors.initials: C
authors.lastname: Baraguey
authors.forename: Michael
authors.initials: M
authors.lastname: Smietana
authors.forename: Jean-Jacques
authors.initials: JJ
authors.lastname: Vasseur
mesh_terms: D001895:Boron / Q000737:chemistry*; D003838:Deoxyadenine Nucleotides / Q000737:chemistry*; D003843:Deoxycytidine Monophosphate / Q000737:chemistry*; D003848:Deoxyguanine Nucleotides / Q000737:chemistry*; D003854:Deoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D014529:Uridine / Q000737:chemistry
chemical_list: D003838:Deoxyadenine Nucleotides; D003848:Deoxyguanine Nucleotides; D003854:Deoxyribonucleotides; D003843:Deoxycytidine Monophosphate; C012873:2'-deoxy-5'-adenosine monophosphate; C007257:2'-deoxyguanosine 5'-phosphate; D001895:Boron; D014529:Uridine