相邻基团参与核酸磷酸三酯的解封闭反应。
Neighbouring group participation in the unblocking of phosphotriesters of nucleic acids.
作者信息
de Rooij J F, Wille-Hazeleger G, Burgers P M, van Boom J H
出版信息
Nucleic Acids Res. 1979;6(6):2237-59. doi: 10.1093/nar/6.6.2237.
Abstract
Two examples of neighbouring group participation during the removal of protecting groups from phosphotriesters of partially or fully protected intermediates of nucleic acids are presented. The first example shows that ammonolysis of aryl groups from phosphotriesters of partially protected - 5'- hydroxy free - nucleic acids (e.g., 4b approximately to; Ar=2C1C 6H4) gives rise to the formation of unnatural nucleic acids (e.g., 7 approximately to and 8 approximately to). The second one illustrates that fluoride ion promoted hydrolysis of 2,2,2-trichloroethyl groups from phosphotriesters of fully protected nucleic acids (e.g., 18a approximately to), having t-butyldimethylsilyl groups at the 2'-positions, leads to the formation of a considerable amount of side-products (e.g., 20 approximately to and 21 approximately to).
摘要
本文给出了两个关于从核酸部分或完全保护中间体的磷酸三酯上去除保护基团过程中邻基参与的例子。第一个例子表明，从部分保护的 - 5'-羟基游离 - 核酸的磷酸三酯（例如，4b 约至；Ar = 2C1C 6H4）上氨解芳基会导致形成非天然核酸（例如，7 约至和 8 约至）。第二个例子说明，在2'-位带有叔丁基二甲基甲硅烷基的完全保护核酸的磷酸三酯（例如，18a 约至）上，氟离子促进的2,2,2 - 三氯乙基基团的水解会导致形成大量副产物（例如，20 约至和 21 约至）。
相似文献
1
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.
2
Fluoride ion catalyzed alkylation of nucleic acid derivatives using trialkyl phosphates, dialkyl sulfates and alkyl methanesulfonates.氟离子催化的使用磷酸三烷基酯、硫酸二烷基酯和甲磺酸烷基酯的核酸衍生物的烷基化反应。
Nucleic Acids Res. 1979;6(6):2261-73. doi: 10.1093/nar/6.6.2261.
3
Complementary addressed modification of nucleic acids with the alkylating derivatives of oligothymidylate ethyl phosphotriesters. Effect of the phosphotriester fragments' configuration.
FEBS Lett. 1988 Aug 15;236(1):243-5. doi: 10.1016/0014-5793(88)80323-5.
4
Studies on the stability of trialkyl phosphates and di-(2'deoxythymidine) phosphotriesters in alkaline and neutral solution. A model study for hydrolysis of phosphotriesters in DNA and on the influence of a beta hydroxyethyl ester group.磷酸三烷基酯和二（2'-脱氧胸苷）磷酸三酯在碱性和中性溶液中的稳定性研究。DNA中磷酸三酯水解及β-羟乙基酯基团影响的模型研究。
Chem Biol Interact. 1986 Oct 15;60(1):57-65. doi: 10.1016/0009-2797(86)90017-7.
5
DFT investigations of phosphotriesters hydrolysis in aqueous solution: a model for DNA single strand scission induced by N-nitrosoureas.密度泛函理论研究水溶液中膦酸三酯的水解：亚硝脲诱导 DNA 单链断裂的模型。
J Mol Model. 2013 Feb;19(2):647-59. doi: 10.1007/s00894-012-1592-z. Epub 2012 Sep 22.
6
Chromatography on Sephadex LH20 as an efficient purification step after removal of internucleotide 2,2,2-trichloroethyl protective groups from oligoribonucleotide phosphotriesters.从寡核糖核苷酸磷酸三酯上去除核苷酸间的2,2,2-三氯乙基保护基团后，使用葡聚糖凝胶LH20进行色谱分离作为一种有效的纯化步骤。
Nucleic Acids Res. 1980 Mar 11;8(5):1097-105. doi: 10.1093/nar/8.5.1097.
7
8
Nucleoside-3'-phosphotriesters as key intermediates for the oligoribonucleotide synthesis. III. An improved preparation of nucleoside 3'-phosphotriesters, their 1H NMR characterization and new conditions for removal of 2-cyanoethyl group.作为寡核糖核苷酸合成关键中间体的核苷-3'-磷酸三酯。III. 核苷3'-磷酸三酯的改进制备方法、其1H NMR表征以及去除2-氰基乙基的新条件。
Nucleic Acids Res. 1976 Dec;3(12):3397-408. doi: 10.1093/nar/3.12.3397.
9
The kinetics of the alkaline hydrolysis of phosphotriesters in DNA.DNA中磷酸三酯的碱性水解动力学
Chem Biol Interact. 1976 May;13(2):151-63. doi: 10.1016/0009-2797(76)90004-1.
10
Chemical synthesis of a messenger ribonucleic acid fragment: AUGUUCUUCUUCUUCUUC.信使核糖核酸片段的化学合成：AUGUUCUUCUUCUUCUUC
Biochemistry. 1982 Mar 2;21(5):1009-18. doi: 10.1021/bi00534a028.
引用本文的文献
1
Chromatography on Sephadex LH20 as an efficient purification step after removal of internucleotide 2,2,2-trichloroethyl protective groups from oligoribonucleotide phosphotriesters.从寡核糖核苷酸磷酸三酯上去除核苷酸间的2,2,2-三氯乙基保护基团后，使用葡聚糖凝胶LH20进行色谱分离作为一种有效的纯化步骤。
Nucleic Acids Res. 1980 Mar 11;8(5):1097-105. doi: 10.1093/nar/8.5.1097.
2
The chemical synthesis of oligoribonucleotides VII. A comparison of condensing agents in the coupling of silylated ribonucleosides.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。
Nucleic Acids Res. 1980 May 10;8(9):2105-15. doi: 10.1093/nar/8.9.2105.
3
Action of acid on oligoribonucleotide phosphotriester intermediates. Effect of released vicinal hydroxy functions.酸对寡核糖核苷酸磷酸三酯中间体的作用。释放的邻位羟基官能团的影响。
Nucleic Acids Res. 1985 Jul 25;13(14):5215-31. doi: 10.1093/nar/13.14.5215.
4
Solid-phase synthesis of branched oligoribonucleotides related to messenger RNA splicing intermediates.与信使核糖核酸剪接中间体相关的支链寡核糖核苷酸的固相合成
Nucleic Acids Res. 1992 Dec 25;20(24):6565-73. doi: 10.1093/nar/20.24.6565.
本文引用的文献
1
The synthesis of oligoribonucleotides. II. Methoxymethylidene derivatives of ribonucleosides and 5'-ribonucleotides.寡核糖核苷酸的合成。II. 核糖核苷和5'-核糖核苷酸的甲氧基亚甲基衍生物。
Tetrahedron. 1967 May;23(5):2301-13. doi: 10.1016/0040-4020(67)80067-x.
2
Studies on polynucleotides. LI. Syntheses of the 64 possible ribotrinucleotides derived from the four major ribomononucleotides.多核苷酸的研究。第一部分。由四种主要核糖单核苷酸衍生而来的64种可能的核糖三核苷酸的合成。
J Am Chem Soc. 1966 Feb 20;88(4):819-29. doi: 10.1021/ja00956a039.
3
The synthesis of oligoribonucleotides-8. The preparation of ribonucleoside 2',5'-bisketals.寡核糖核苷酸的合成-8。核糖核苷2',5'-双缩酮的制备。
Tetrahedron. 1970 Feb;26(4):1031-41. doi: 10.1016/s0040-4020(01)98780-0.
4
4-methoxytetrahydropyran-4-yl. A symmetrical alternative to the tetrahydropyranyl protecting group.4-甲氧基四氢吡喃-4-基。四氢吡喃基保护基团的一种对称替代物。
Tetrahedron. 1970 Feb;26(4):1023-30. doi: 10.1016/s0040-4020(01)98779-4.
5
The synthesis of oligoribonucleotides. X. Preparation of 2',3'-cyclic phosphates of ribonucleosides and diribonucleoside phosphates via phosphotriester intermediates.寡核糖核苷酸的合成。X. 通过磷酸三酯中间体制备核糖核苷2',3'-环磷酸酯和二核糖核苷磷酸酯。
J Chem Soc Perkin 1. 1973;21:2513-7. doi: 10.1039/p19730002513.
6
[New synthesis of nucleotide analogues of 5'-amino-5'-desoxy-nucleosides].[5'-氨基-5'-脱氧核苷的核苷酸类似物的新合成方法]
Chem Ber. 1972;105(3):991-9. doi: 10.1002/cber.19721050330.
7
Aqueous solution conformation of rigid nucleosides and nucleotides.刚性核苷和核苷酸的水溶液构象
J Am Chem Soc. 1976 Jun 9;98(12):3541-8. doi: 10.1021/ja00428a026.
8
Improved triester approach for the synthesis of pentadecathymidylic acid.用于合成十五聚胸苷酸的改进三酯法。
J Am Chem Soc. 1975 Dec 10;97(25):7327-32. doi: 10.1021/ja00858a020.
9
Conformational properties of dinucleoside monophosphates in solution: dipurines and dipyrimidines.溶液中二磷酸核苷的构象性质：双嘌呤和双嘧啶。
Biochemistry. 1976 Aug 10;15(16):3627-39. doi: 10.1021/bi00661a034.
10
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.
Zotero 插件