- Expanding the borononucleotide family: synthesis of borono-analogues of dCMP, dGMP and dAMP. doi link

Auteur(s): Martin A., Mohanan Kishor, Luvino Delphine, Floquet N., Baraguey C., Smietana M., Vasseur J.-J.

(Article) Publié: Organic & Biomolecular Chemistry / Organic And Biomolecular Chemistry, vol. 7 p.4369-4377 (2009)

Ref HAL: hal-01109915_v1
DOI: 10.1039/b912616c

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.