396123-73-2Relevant academic research and scientific papers
Synthesis of enzymatically and chemically non-hydrolyzable analogues of dinucleoside triphosphates Ap3A and Gp3G
Klein, Emmanuel,Mons, Stephane,Valleix, Alain,Mioskowski, Charles,Lebeau, Luc
, p. 146 - 153 (2007/10/03)
Dinucleoside polyphosphates are ubiquitous compounds tightly involved in the regulation of a number of key biological processes. Hydrolysis-resistant analogues of Ap3A and Gp3G, two important members of that family of nucleotides, have been synthesized. P1,P2.P2,P3-Bis-methylene diadenosine and diguanosine triphosphates were prepared from O,O-dialkyl methaneselenophosphonates using an original methodology. Whereas the 2-fold addition of the methanephosphonate anion to the activated phosphorus species cannot be performed, multiple condensation of lithiated methaneselenophosphonate with electrophilic trivalent phosphorus compounds is revealed to be very effective. A one-pot condensation/esterification/oxidation sequence involving O,O-dialkyl methaneselenophosphonates provides a highly efficient route to the PCH2PCH2P backbone. This new development in selenophosphonate chemistry offers a great potential for further regioselective functionalization of polyphosphate mimics.
