Stereochemistry of the mammalian adenylate cyclase reaction.
Adenosine 5'-O-(1-thiotriphosphate), Sp-diastereomer, is cyclized by adenylate cyclase from bovine brain to adenosine 3',5'-cyclic phosphorothioate, Rp diastereomer, establishing inversion of configuration for this reaction. This result can most easily be explained by a direct nucleophilic attack of the 3'-OH group on alpha-phosphorus without involving a covalent enzyme intermediate.
D000255:Adenosine Triphosphate / Q000031:analogs & derivatives; D000262:Adenylyl Cyclases / Q000378:metabolism*; D000818:Animals; D001921:Brain / Q000201:enzymology; D002417:Cattle; D002462:Cell Membrane / Q000201:enzymology; D013237:Stereoisomerism; D013873:Thionucleotides
D013873:Thionucleotides; C017817:adenosine 5'-(1-thio)triphosphate; D000255:Adenosine Triphosphate; D000262:Adenylyl Cyclases