Prebiotic synthesis and reactions of nucleosides and nucleotides.
Diiminosuccinonitrile (DISN) has been investigated as a potential prebiotic phosphorylating agent. It is formed readily by the oxidation of diaminomaleonitrile (DAMN), a tetramer of HCN. DISN effects the cyclization of 3'-adenosine monophosphate to adenosine 2',3'-cyclic phosphace in up to 40% yield. The DISN-mediated phosphorylation of uridine to uridine mono-phosphate does not proceed efficiently in aqueous solution. The reaction of DISN and BrCN with uridine-5'-phosphate and uridine results in the formation of 2,2'-anhydronucleotides and 2,2'-anhydronucleosides respectively, and other reaction products resulting from an initial reaction at the 2'- and 3'-hydroxyl groups. The clay mineral catalysis of the cyclization of adenosine-3'-phosphate was investigated using homoionic montmorillonites.
Ferris
J P
JP
Department of Chemistry, Rennselaer Polytechnic Institute, Troy, NY 12181, USA.
Yanagawa
H
H
Hagan
W J
WJ
D000249:Adenosine Monophosphate / Q000737:chemistry*; D001546:Bentonite; D002384:Catalysis; D019418:Evolution, Chemical; D019143:Evolution, Molecular; D009570:Nitriles / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D010766:Phosphorylation; D014529:Uridine / Q000737:chemistry*; D014542:Uridine Monophosphate / Q000138:chemical synthesis / Q000737:chemistry
D009570:Nitriles; D009705:Nucleosides; D009711:Nucleotides; D001546:Bentonite; C047926:diiminosuccinonitrile; D000249:Adenosine Monophosphate; D014542:Uridine Monophosphate; D014529:Uridine