Synthesis And Physicochemical Properties Of Polynucleotide Analogues Containing Pyrimidine Bases

Polynucleotide analogues containing pyrimidine (uracil and thymine) bases, poly[(1'-beta-uracil-1-yl-2',5'-dideoxy-D-glycero-pent-4'-enofuranose)-alt-(maleic acid)] (12) and poly[(1'-beta-thymin-1-yl-2',5'-dideoxy-D-glycero-pent-4'-enofuranose)-alt-(maleic acid)] (15), were synthesized by the alternating copolymerization of relevant nucleoside derivatives and maleic anhydride, and the subsequent hydrolysis. The polymers had quite similar structures to the natural polymers and were soluble in water. They showed high hypochromicities up to 49% and excimer fluorescence due to the base stacking, and polyelectrolyte behavior. Since the polymers had compact structures, depyrimidinations, the release of pyrimidine bases from the polymer backbone, occurred in aqueous solutions with higher rates compared with those of the natural polymers.