Uranyl ion catalyzes the polymerization of adenosine-5′-phosphorimidazolide very efficiently in aqueous solution. Up to 95% of the input adenosine-5′-phosphorimidazolide is converted to oligoadenylates from dimer to hexadecamer when 1 mM of UO22+ is used as a catalyst. The oligomeric products are predominantly 2′–5′ linked. The chain length and the regioselectivity of the resulting oligoadenylates varies greatly with the concentration of the UO22+ ion catalyst and the pH of the reaction medium. A high total yield of oligouridylates up to dodecamer is also obtained by UO22+ ion catalyst with high 2′–5′ regioselectivity. The oligonucleotide formation is mediated by UO22+-nucleotide complex.
Uranyl ion catalyses the oligomerization of cytidine-5'-phosphoroimidazolide in aqueous solution, yielding 3'-5'-linked cyclic diand tri-cytidylates preferentially at high catalyst concentration, or 2'-5'linked linear oligocytidylates at lower catalyst concentration. Addition of Ag + affects the uranyl ion-catalysed oligocytidylate formation and alters the product distribution.A series of reactions of activated nucleotides in aqueous solution provides a non-enzymatic model of nucleic acid biosynthesis,' and affords a new attractive synthetic method for oligonu~leotides.~*~ Nucleoside 5'-phosphoroimidazolide, an
Various adenosine-5′-phosphorazolides were prepared from adenosine-5′-phosphate and azoles such as 2-methylimidazole, 4-methylimidazole, 1,2,4-triazole, 3-nitro-1,2,4-triazole, benzimidazole and 2-methylbenzimidazole. The adenosine-5′-phosphorazolides obtained were then polymerized in neutral aqueous solution using uranyl(VI) ion as a catalyst. Oligoadenylates up to the hexadecamer with 2′-5′-internucleotide linkage were formed in high yields under the optimum condition. The azoles worked as adenylate activating group, and had a large effect on the rate of polymerization, the yield and the chain length of the resulting oligonucleotides. Imidazolides showed the moderate reactivity and gave oligoadenylates of the longest chain length. From the phosphortriazolides, only short-chained oligoadenylates were obtained, as they are susceptible to the hydrolysis. Polymerization and hydrolysis reaction of the benzimidazolides were retarded.
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