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
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
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DOI：
10.1021/ja9700764
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发表时间：
1997-05-14
影响因子：
15
通讯作者：
Ferris, JP
中科院分区：
文献类型：
--
作者：
Prabahar, KJ;Ferris, JP
合成了5'-单磷酸腺苷(5'-AMP)和5'-单磷酸尿苷(5'-UMP)的甲基腺嘌呤和腺嘌呤N-磷酰基衍生物，并阐明了它们的结构。研究了腺苷5'-氨基磷酸酯的腺嘌呤衍生物在蒙脱石上的齐聚反应。蒙脱石上的1-甲基腺嘌呤和3-甲基腺嘌呤衍生物产生长达十一聚体的寡腺苷酸，蒙脱石上的2-甲基腺嘌呤和腺嘌呤衍生物分别产生高达六聚体和五聚体的低聚物。 1-甲基腺嘌呤衍生物产生线性、环状和 A(5')ppA 衍生的寡核苷酸，对 3',5'-磷酸二酯键的区域选择性平均为 84%。讨论了磷酸活化基团的pK(a)和胺结构对蒙脱石催化腺苷S-氨基磷酸酯齐聚反应的影响。描述了腺苷的甲基腺嘌呤和腺嘌呤 N-磷酰基衍生物的结合和反应。
Methyladenine and adenine N-phosphoryl derivatives of adenosine 5'-monophosphate (5'-AMP) and uridine 5'-monophosphate (5'-UMP) are synthesized, and their structures are elucidated. The oligomerization reactions of the adenine derivatives of 5'-phosphoramidates of adenosine on montmorillonite are investigated. 1-Methyladenine and 3-methyladenine derivatives on montmorillonite yielded oligoadenylates as long as undecamer, and the 2-methyladenine and adenine derivatives on montmorillonite yielded oligomers up to hexamers and pentamers, respectively. The 1-methyladenine derivative yielded linear, cyclic, and A(5')ppA-derived oligonucleotides with a regioselectivity for the 3',5'-phosphodiester linkages averaging 84%. The effect of pK(a) and amine structure of phosphate-activating groups on the montmorillonite-catalyzed oligomerization of the S-phosphoramidate of adenosine are discussed. The binding and reaction of methyladenine and adenine N-phosphoryl derivatives of adenosine are described.