Issue 21, 2009

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 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.

Graphical abstract: Expanding the borononucleotide family: synthesis of borono-analogues of dCMP, dGMP and dAMP

Supplementary files

Article information

Article type
Paper
Submitted
26 Jun 2009
Accepted
03 Aug 2009
First published
27 Aug 2009

Org. Biomol. Chem., 2009,7, 4369-4377

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

A. R. Martin, K. Mohanan, D. Luvino, N. Floquet, C. Baraguey, M. Smietana and J. Vasseur, Org. Biomol. Chem., 2009, 7, 4369 DOI: 10.1039/B912616C

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