Synthesis of a nucleoside hapten with a [P(O)-O-N] linkage to elicit catalytic antibodies with phosphodiesterase activity

The nucleoside analogue 1 incorporating a [P(O)-O-N] linkage was synthesized as a hapten to obtain catalytic antibodies that may cleave a phosphodiester bond. Secondary alcohol 15 was successfully phosphorylated with the phosphodiester derived from hydroxylamine derivative 7b to give a protected form of the hapten. Deprotection was accomplished using Pd-catalyzed deallylation that afforded hapten 1 after HPLC purification.