2',3'-SECO PYRIMIDINE NUCLEOSIDES AND NUCLEOTIDES, INCLUDING STRUCTURAL ANALOGS OF 3'-5'-CYCLIC CMP AND UMP, AND THEIR BEHAVIOR IN SEVERAL ENZYME-SYSTEMS

Cyclization of 2'',3''-seco-5''- CMP and UMP with dicyclohexylcarbodiimide leads to 2'',3''-seco-3'':5''- cCMP and cUMP, formal structural analogues of 3'':5''-cCMP and cUMP. POCl3 phosphorylation of 2'',3''-secocytidine gave the same product in 50% yield, plus three additional seco nucleotides, one of which was independently obtained by enzymatic phosphorylation with the wheat shoot phosphotransferase system. The behavior of these nucleotides has been examined in several enzyme systems. In particular, the seco 3'':5''-cyclic phosphates are resistant to beef heart cyclic nucleotide phosphodiesterase, but are slowly hydrolyzed to the monophosphates by higher plant cyclic nucleotide phosphodiesterase.