384375-15-9Relevant 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.
Direct α-chlorination of O,O-dialkyl chalcogenophosphonates with phosphorus oxychloride
Mons, Stéphane,Sabourault, Nicolas,Klein, Emmanuel,Mioskowski, Charles,Lebeau, Luc
, p. 7547 - 7549 (2007/10/03)
α-Chlorination of phosphonates, and O,O-dialkyl thio- and selenophosphonates involving the direct reaction of their lithiated anion with phosphorus oxychloride is described. The reaction gives good results where previously known methods fail. The role of the chalcogen atom, and the influence of the nature of the alkyl chain with respect to the reactivity are discussed.
