Studies on bovine adrenal estrogen sulfotransferase. III. Facile synthesis of 3'-phospho- and 2'-phosphoadenosine 5'-phosphosulfate.
A practical synthesis of 3'-phosphoadenosine 5'-phosphosulfate (IV) in yields of 68-72% from adenosine 2',3'-cyclic phosphate 5'-phosphate (II) is described. Reaction of II with triethylamine-N-sulfonic acid affords adenosine 2',3'-cyclic phosphate 5'-phosphosulfate (III) which, on treatment with ribonuclease-T2, provides IV. Spleen phosphodiesterase, on the other hand, converts III to 2'-phosphoadenosine 5'-phosphosulfate (V). The biological activity of IV, measured by sulfate transfer to [6,7-3H2]estrone as mediated by bovine adrenal estrone sulfotransferase (3'-phosphoadenylyl-sulfate:estrone 3-sulfotransferase, EC 2.8.2.4), is identical with that obtained with a sample of IV prepared by an established biochemical procedure. By contrast, V exhibits approximately one-third the activity of the natural isomer.
D000227:Adenine Nucleotides / Q000138:chemical synthesis*; D000249:Adenosine Monophosphate / Q000031:analogs & derivatives; D000311:Adrenal Glands / Q000201:enzymology*; D000818:Animals; D002417:Cattle; D055598:Chemical Phenomena; D002621:Chemistry; D000242:Cyclic AMP / Q000031:analogs & derivatives; D004970:Estrone / Q000378:metabolism; D010724:Phosphoadenosine Phosphosulfate / Q000138:chemical synthesis*; D010727:Phosphoric Diester Hydrolases / Q000378:metabolism; D012260:Ribonucleases / Q000378:metabolism; D013466:Sulfurtransferases / Q000378:metabolism*
D000227:Adenine Nucleotides; D004970:Estrone; D000249:Adenosine Monophosphate; C013794:adenosine 2',3'-cyclic phosphate 5'-phosphate; D010724:Phosphoadenosine Phosphosulfate; D000242:Cyclic AMP; D013466:Sulfurtransferases; D012260:Ribonucleases; D010727:Phosphoric Diester Hydrolases