Synthesis of 8-vinyladenosine 5′-di- and 5′-triphosphate:: evaluation of the diphosphate compound on ribonucleotide reductase

The synthesis of 5'-di- and 5'-triphosphate of 8-vinyladenosine to be tested on ribonucleotide reductases requires the modification of known methods. The phosphate group was introduced by treatment with an in situ generated chlorophosphite. Protection of the 2',3' diol with acetyl groups suppressed depurination during acid removal of the phosphotriester protecting groups. The di- and triphosphate compounds were obtained by treatment of the activated adenylic acid with phosphate or pyrophosphate anions followed by removal of the acetate protecting groups. Preliminary studies were conducted on Escherichia coli ribonucleotide reductase and have shown that the diphosphate compound is efficiently reduced. (C) 2003 Elsevier Ltd. All rights reserved.