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Paper
Org. Biomol. Chem., 2009, 7, 4369 - 4377, DOI: 10.1039/b912616c
Expanding the borononucleotide family: synthesis of borono-analogues of dCMP, dGMP and dAMP
Anthony R. Martin, Kishor Mohanan, Delphine Luvino, Nicolas Floquet, Carine Baraguey, Michael Smietana and Jean-Jacques Vasseur
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 1H 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.
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