Enzymatic synthesis of vinyl uridine esters catalyzed by Bioprase, alkaline protease from Bacillus subtilis

Abstract

Enzyme screening was examined on the transesterification of pyrimidine nucleoside, uridine, and divinyladipate. Among the 12 different types of industrial grade enzymes, Bioprase conc., a protease from Bacillus subtilis, showed the highest regioselective acylation activity. And two kinds of uridine vinyl esters were prepared via transesterification using uridine with divinyl adipate and divinyl sebacate catalyzed by the Bioprase conc. in dimethylformamide. According to 13C NMR analysis, acylation occurred at the 5′-position of the hydroxyl group of ribofuranose in uridine to give 5′- O-vinyl adipoyl uridine and 5′- O-vinyl sebacoyl uridine. These resulting monomers were polymerized in dimethylsulfoxide by azobisisobutyronitrile to give polymers.