寡核糖核苷酸的化学合成VII. 甲硅烷基化核糖核苷偶联中缩合剂的比较。
The chemical synthesis of oligoribonucleotides VII. A comparison of condensing agents in the coupling of silylated ribonucleosides.
作者信息
Ogilvie K K, Pon R T
出版信息
Nucleic Acids Res. 1980 May 10;8(9):2105-15. doi: 10.1093/nar/8.9.2105.
Abstract
The t-butyldimethylsilyl group is shown to be an ideal protecting group for the 2T-hydroxyl function of ribonucleosides during the synthesis of ribonucleotides using any of nine commonly used condensing agents. The phosphite coupling procedure compares favorably with all of the widely used condensing agents and provides a most convenient route to the key intermediates in the "modified" triester strategy.
摘要
在使用九种常用缩合剂中的任何一种合成核糖核苷酸的过程中，叔丁基二甲基硅烷基被证明是核糖核苷2'-羟基功能的理想保护基团。亚磷酸酯偶联方法与所有广泛使用的缩合剂相比具有优势，并为“改良”三酯策略中的关键中间体提供了一条非常便捷的途径。
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本文引用的文献
1
Deoxy oligonucleotide synthesis via the triester method.通过三酯法合成脱氧寡核苷酸。
J Org Chem. 1973 Jan 26;38(2):245-50. doi: 10.1021/jo00942a011.
2
Synthesis of thymidine oligonucleotides by phosphite triester intermediates.通过亚磷酸三酯中间体合成胸苷寡核苷酸。
J Am Chem Soc. 1976 Jun 9;98(12):3655-61. doi: 10.1021/ja00428a045.
3
Synthesis of oligoribonucleotides.寡核糖核苷酸的合成
J Am Chem Soc. 1977 Nov 9;99(23):7741-3. doi: 10.1021/ja00465a073.
4
The chemical synthesis of the anticodon loop of an eukaryotic initiator tRNA containing the hypermodified nucleoside N6-/N-threonylcarbonyl/-adenosine/t6A/1.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。
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Neighbouring group participation in the unblocking of phosphotriesters of nucleic acids.相邻基团参与核酸磷酸三酯的解封闭反应。
Nucleic Acids Res. 1979;6(6):2237-59. doi: 10.1093/nar/6.6.2237.
6
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