Selective Removal of Protecting Groups for Phosphomonoesters of Nucleotides by Anodic Oxidation

Abstract

Cyclic volutammetry of phenyl derivatives of various nucleotides was carried out, using the parent nucleosides as a control. The p-N-benzylaminophenyl ester of 3'-O-acetylthymidine 5'-phosphate showed a peak at low anodic potential, and the N-benzyl-aminophenyl group could be removed by controlled potential electrolysis at this potential. p-N-Tritylaminophenyl-, p-N-acetylaminophenyl and p-methoxyphenyl esters of nucleotides were also subjected to controlled potential electrolysis ; the oxidative removal of these phenyl groups was less effective than that of the N-benzylaminophenyl ester.