包含超修饰核苷N6-（N-苏氨甲酰）-腺苷（t6A）的真核起始tRNA反密码子环的化学合成。
The chemical synthesis of the anticodon loop of an eukaryotic initiator tRNA containing the hypermodified nucleoside N6-/N-threonylcarbonyl/-adenosine/t6A/1.
作者信息
Adamiak R W, Biała E, Grześkowiak K, Kierzek R, Kraszewski A, Markiewicz W T, Okupniak J, Stawiński J, Wiewiórowski M
出版信息
Nucleic Acids Res. 1978 Jun;5(6):1889-905. doi: 10.1093/nar/5.6.1889.
Abstract
In this work, the first example of chemical synthesis of oligoribonucleotide containing the hypermodified nucleoside N6-/N-threonylcarbonyl/-adenosine /t6A/ is presented. Synthesis of the heptamer C-C-C-A-U-t6A-A IX, the sequence of which is related to the anticodon loop of the initiator tRNA from yellow lupine, was achieved by: /i/ phosphotriester block synthesis of suitably protected heptamer VI containing an adenosine unit with a free exo-NH2 group, /ii/ highly effective "one-flask" procedure for the transformation of the free exo-NH2 group of adenosine unit of heptamer VI into a N,N'-disubstituted urea system of t6A of heptamer VII /hypermodification/, and /iii/ final deprotection of VIII /32% total yield/ with the use of a new approach for simultaneous hydrogenolysis /PdO-hydrogen-pyridine/ of the p-nitrobenzyl group and 2,2,2-trichloroethyl groups from carboxyl function of t6A and internucleotide phosphates respectively.
摘要
在本工作中，展示了化学合成含超修饰核苷N6-/N-苏氨甲酰/-腺苷（t6A）的寡核糖核苷酸的首个实例。通过以下步骤实现了七聚体C-C-C-A-U-t6A-A IX的合成，其序列与来自黄羽扇豆的起始tRNA的反密码子环相关：/i/ 对含有游离外氨基的腺苷单元的合适保护的七聚体VI进行磷酸三酯片段合成；/ii/ 将七聚体VI的腺苷单元的游离外氨基高效“一锅法”转化为七聚体VII的t6A的N,N'-二取代脲系统（超修饰）；以及/iii/ 采用一种新方法，同时从t6A的羧基官能团和核苷酸间磷酸酯分别氢解对硝基苄基和2,2,2-三氯乙基，对VIII进行最终脱保护（总产率32%）。
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