Nucleoside und Nucleotide,Teil 12. Synthese von Dinucleosidmonophosphaten mit 1-(2′-Desoxy-β-D-ribofuranosyl)-2(1H)-pyrimidon als Baustein

Nucleosides and Nucleotides. Part 12. Synthesis of Dinucleoside Monophosphates Containing 1-(2′-Deoxy-β-D -ribofuranosyl)-2(1H)-pyrimidone The connexion of the modified nucleoside 1-(2′-deoxy-β-D -ribofuranosyl)-2(1H)-pyrimidone (M_d, 2 ) with the natural nucleotides pT_d and pG_d is described. The protected dinucleoside monophosphates (MeOTr)M_dpT_d ( 6 ) and (MeOTr)M_dpG ( 9 ) were prepared by the standard phosphodiester method using DCC as condensing agent. M_dpT_d ( 7 ) was obtained by treatment of 6 with formic acid/methanol 7 : 3 at 0° 9 was converted to the free dinucleoside monophosphate M_dpG_d ( 11 ) by removing the N-isobutyryl- and p-methoxytrityl protecting group on consecutive treatment with 0.04N CH₃ONa in CH₃OH and HCOOH/CH₃OH 7:3 at 0° respectively. Enzymatic degradation of the free dinucleoside of the free dinucleoside monophosphates 7 and 11 yielded the corresponding nucleosides and nucleotides in the correct ratios.