Expanding the borononucleotide family: synthesis of borono-analogues of dCMP, dGMP and dAMP.
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.
Martin
Anthony R
AR
Institut des Biomolécules Max Mousseron, UMR 5247 CNRS-Université Montpellier 1, place Eugène Bataillon, 34095 Montpellier, France.
Mohanan
Kishor
K
Luvino
Delphine
D
Floquet
Nicolas
N
Baraguey
Carine
C
Smietana
Michael
M
Vasseur
Jean-Jacques
JJ
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
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