2',5'-Oligoadenylates and related 2',5'-oligonucleotide analogs. 1. Enzymic synthesis and substrate specificity of the interferon-induced murine 2',5'-oligoadenylate synthetase

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Abstract
The substrate specificity of the interferon-induced mouse [neoplastic fibroblast] L cell enzyme, 2'',5''-oligoadenylate synthetase, was determined with a number of nucleoside 5''-triphosphate analogs. Selected nucleoside 5''-triphosphates were converted to 2'',5''-oligonucleotides with the following order of efficiency for the nucleoside: 8-azaadenosine > adenosine = 2-chloroadenosine > sangivamycin > toyocamycin > formycin > 3-ribosyladenine > ribavirin > tubercidin > adenosine 1-oxide > 2-.beta.-D-ribofuranosylthiazole-4-carboxamide > inosine = 1,N6-ethenoadenosine > guanosine > 8-bromoadenosine = uridine > cytidine. Adenosine 5''-(.beta.,.gamma.-imidotriphosphate) did not seem to be a recognizable substrate since no detectable product resulted. Either the 2'',5''-oligoadenylate synthetase is not as specific as had been previously thought, or there may be more than one 2'',5''-oligonucleotide synthetase. The 2'',5''-oligonucleotide analog products in which the adenosine of ppp(A2''p5'')nA (5''-triphosphooligo[(2''-5'')adenylyl]adenosine) was replaced by the various nucleoside analogs were separated by DEAE-cellulose column chromatography and the chain length and number of 5''-phosphate residues analyzed by a rapid, efficient high-performance liquid chromatographic system involving ion-pairing C18 reversed-phase column chromatography. Separation of the 5''-mono-, 5''-di- and 5''-triphosphorylated forms of the 2'',5''-oligonucleotide analog dimers, trimers, tetramers and pentamers was readily achieved by this useful HPLC system. No 5''-nonphosphorylated forms were detected for any of the 2'',5''-oligonucleotide analog products.

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