Adenine derivatives as phosphate-activating groups for the regioselective formation of 3',5'-linked oligoadenylates on montmorillonite: possible phosphate-activating groups for the prebiotic synthesis of RNA.

摘要: Methyladenine and adenine N-phosphoryl derivatives of adenosine 5'-monophosphate (5'-AMP) uridine (5'-UMP) are synthesized, their structures elucidated. The oligomerization reactions the 5'-phosphoramidates on montmorillonite investigated. 1-Methyladenine 3-methyladenine yielded oligoadenylates as long undecamer, 2-methyladenine oligomers up to hexamers pentamers, respectively. 1-methyladenine derivative linear, cyclic, A5'ppA-derived oligonucleotides with a regioselectivity for 3',5'-phosphodiester linkages averaging 84%. effect pKa amine structure phosphate-activating groups montmorillonite-catalyzed 5'-phosphoramidate discussed. binding reaction methyladenine described.