Rapid oxidative-elimination of the terminal base from model deoxynucleotide esters

The 5'-isopropyl esters of 2'-deoxycytidylate, 2'-deoxyadenylate, 2'-deoxyguanylate and 2'-deoxythymidylate were synthesized and used as model substrates to demonstrate that the 3'-terminal deoxynucleoside can be rapidly removed by combined 3'-hydroxyl oxidation and beta-elimination. Trifluoroacetyloxy-dimethylsulfonium ion oxidation of the free 3'-hydroxyl group gave almost 80% yields of the free purine and pyrimidine bases in less than 5 minutes reaction at -80 degrees C.