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.
Health and Safety Research Division, Oak Ridge National Laboratory, TN 37831-6101.
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D000089:Acetic Anhydrides; D001483:Base Sequence; D003854:Deoxyribonucleotides; D004952:Esters; D010084:Oxidation-Reduction; D013452:Sulfonium Compounds; D014269:Trifluoroacetic Acid
D000089:Acetic Anhydrides; D003854:Deoxyribonucleotides; D004952:Esters; D013452:Sulfonium Compounds; C060745:trifluoroacetyloxydimethylsulfonium; D014269:Trifluoroacetic Acid