boron has been researched along with 2--deoxyguanosine-5--phosphate* in 1 studies
1 other study(ies) available for boron and 2--deoxyguanosine-5--phosphate
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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. Topics: Boron; Deoxyadenine Nucleotides; Deoxycytidine Monophosphate; Deoxyguanine Nucleotides; Deoxyribonucleotides; Magnetic Resonance Spectroscopy; Models, Molecular; Molecular Conformation; Uridine | 2009 |