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1
Synthesis of nucleic acid methylphosphonates via the 1-hydroxybenzotriazole phosphotriester approach.通过1-羟基苯并三唑磷酸三酯法合成核酸甲基膦酸酯。
Nucleic Acids Res. 1986 Mar 11;14(5):2171-85. doi: 10.1093/nar/14.5.2171.
2
A general method for the synthesis of 5'-monophosphates of DNA fragments via phosphotriester intermediates.一种通过磷酸三酯中间体合成DNA片段5'-单磷酸酯的通用方法。
Nucleic Acids Res. 1982 Apr 10;10(7):2337-51. doi: 10.1093/nar/10.7.2337.
3
An approach to the stereoselective synthesis of Sp-dinucleoside phosphorothioates using phosphotriester chemistry.一种利用磷酸三酯化学方法立体选择性合成 Sp-二核苷硫代磷酸酯的途径。
Nucleic Acids Res. 1987 Dec 10;15(23):9921-32. doi: 10.1093/nar/15.23.9921.
4
Polymer supported DNA synthesis using hydroxybenzotriazole activated phosphotriester intermediates.使用羟基苯并三唑活化的磷酸三酯中间体进行聚合物支持的DNA合成。
Nucleic Acids Res. 1984 Nov 26;12(22):8639-51. doi: 10.1093/nar/12.22.8639.
5
Synthesis of oligonucleotide having a bent structure by incorporation of an interresidually cyclized uridylyl (3'-5')uridine unit.通过掺入残基间环化的尿苷酰（3'-5'）尿苷单元合成具有弯曲结构的寡核苷酸。
Nucleic Acids Symp Ser. 1995(34):181-2.
6
Synthesis of cyclic oligonucleotides by a modified phosphotriester approach.通过改良的磷酸三酯法合成环状寡核苷酸。
Nucleic Acids Res. 1988 May 25;16(10):4607-20. doi: 10.1093/nar/16.10.4607.
7
Synthesis of ppTppp via phosphotriester intermediates.通过磷酸三酯中间体合成ppTppp。
Nucleic Acids Res. 1983 Nov 11;11(21):7545-54. doi: 10.1093/nar/11.21.7545.
8
Synthesis of short RNA fragments by the benzotriazolyl phosphotriester approach.通过苯并三唑基磷酸三酯法合成短RNA片段。
Nucleic Acids Res. 1983 Dec 10;11(23):8389-405. doi: 10.1093/nar/11.23.8389.
9
Synthesis of phosphorothioate-containing DNA fragments by a modified hydroxybenzotriazole phosphotriester approach.通过改良的羟基苯并三唑磷酸三酯方法合成含硫代磷酸酯的DNA片段。
Nucleic Acids Res. 1984 Dec 11;12(23):9095-110. doi: 10.1093/nar/12.23.9095.
10
Synthesis and properties of dithymidine phosphate analogues containing 3'-thiothymidine.含3'-硫代胸苷的二磷酸胸苷类似物的合成与性质
Nucleic Acids Res. 1990 Feb 25;18(4):829-35. doi: 10.1093/nar/18.4.829.

引用本文的文献

1
The application of the AMB protective group in the solid-phase synthesis of methylphosphonate DNA analogues.AMB保护基团在甲基膦酸酯DNA类似物固相合成中的应用。
Nucleic Acids Res. 1993 Jul 25;21(15):3493-500. doi: 10.1093/nar/21.15.3493.
2
Synthesis of (3'-5'),(2'-5')-linked di- and tri-adenylyl methylphosphonate analogs.（3'-5'），（2'-5'）连接的二腺苷基和三腺苷基甲基膦酸酯类似物的合成
Nucleic Acids Res. 1993 Jul 11;21(14):3245-8. doi: 10.1093/nar/21.14.3245.
3
A new approach to the synthesis of the 5'-deoxy-5'-methylphosphonate linked thymidine oligonucleotide analogues.一种合成5'-脱氧-5'-甲基膦酸酯连接的胸腺嘧啶寡核苷酸类似物的新方法。
Nucleic Acids Res. 1995 Mar 25;23(6):893-900. doi: 10.1093/nar/23.6.893.
4
Synthesis of nucleic acid methylphosphonothioates.核酸甲基硫代磷酸酯的合成。
Nucleic Acids Res. 1988 Aug 11;16(15):7633-45. doi: 10.1093/nar/16.15.7633.

本文引用的文献

1
Some observations relating to the oximate ion promoted unblocking of oligonucleotide aryl esters.一些与肟离子促进寡核苷酸芳基酯解封闭相关的观察结果。
Nucleic Acids Res. 1981 Sep 25;9(18):4611-26. doi: 10.1093/nar/9.18.4611.
2
Oligothymidylate analogues having stereoregular, alternating methylphosphonate/phosphodiester backbones as primers for DNA polymerase.具有立体规则交替甲基膦酸酯/磷酸二酯主链的寡胸苷酸类似物作为DNA聚合酶的引物。
Biochemistry. 1982 May 11;21(10):2507-12. doi: 10.1021/bi00539a033.
3
Biochemical and biological effects of nonionic nucleic acid methylphosphonates.非离子型核酸甲膦酸酯的生化及生物学效应
Biochemistry. 1981 Mar 31;20(7):1874-80. doi: 10.1021/bi00510a024.
4
Methylphosphonates as probes of protein-nucleic acid interactions.甲基膦酸酯作为蛋白质 - 核酸相互作用的探针。
Nucleic Acids Res. 1984 Apr 11;12(7):3387-404. doi: 10.1093/nar/12.7.3387.
5
Synthesis of phosphorothioate-containing DNA fragments by a modified hydroxybenzotriazole phosphotriester approach.通过改良的羟基苯并三唑磷酸三酯方法合成含硫代磷酸酯的DNA片段。
Nucleic Acids Res. 1984 Dec 11;12(23):9095-110. doi: 10.1093/nar/12.23.9095.
6
Synthesis of short RNA fragments by the benzotriazolyl phosphotriester approach.通过苯并三唑基磷酸三酯法合成短RNA片段。
Nucleic Acids Res. 1983 Dec 10;11(23):8389-405. doi: 10.1093/nar/11.23.8389.
7
Polymer supported DNA synthesis using hydroxybenzotriazole activated phosphotriester intermediates.使用羟基苯并三唑活化的磷酸三酯中间体进行聚合物支持的DNA合成。
Nucleic Acids Res. 1984 Nov 26;12(22):8639-51. doi: 10.1093/nar/12.22.8639.
8
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.
9
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.
10
Characterization of sequence-specific oligodeoxyribonucleoside methylphosphonates and their interaction with rabbit globin mRNA.序列特异性寡脱氧核糖核苷甲基膦酸酯的表征及其与兔珠蛋白mRNA的相互作用。
Biochemistry. 1985 Jul 16;24(15):4041-6. doi: 10.1021/bi00336a036.

通过1-羟基苯并三唑磷酸三酯法合成核酸甲基膦酸酯。

Synthesis of nucleic acid methylphosphonates via the 1-hydroxybenzotriazole phosphotriester approach.

作者信息

Marugg J E, de Vroom E, Dreef C E, Tromp M, van der Marel G A, van Boom J H

出版信息

Nucleic Acids Res. 1986 Mar 11;14(5):2171-85. doi: 10.1093/nar/14.5.2171.

DOI:10.1093/nar/14.5.2171
PMID:3457366
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC339650/
Abstract

Dinucleoside methylphosphonates can easily be prepared starting from properly protected d-nucleosides and the bifunctional phosphorylating reagent methyl-O,O-bis(1-benzotriazolyl)phosphate. Separation of the diastereoisomers of 5'-DMTR-d-Ap(Me)T-3'-lev affords optically pure dinucleoside methylphosphonates which, after removal of the 3'-levulinoyl group, have been used for the synthesis of the two optically pure diastereoisomers of the hexamer d-CpGpAp(Me)TpCpG. Further, a one-pot procedure for the preparation of uridine-3',5'-cyclic methylphosphonate will be described. We also found that 3',5'-methylphosphonate linkages in RNA are not stable towards mild acid treatment.

摘要

从适当保护的d-核苷和双功能磷酸化试剂甲基-O,O-双(1-苯并三唑基)磷酸酯开始，可以很容易地制备二核苷甲基膦酸酯。5'-DMTR-d-Ap(Me)T-3'-乙酰丙酸酯的非对映异构体的分离得到了光学纯的二核苷甲基膦酸酯，在除去3'-乙酰丙酰基后，它们被用于合成六聚体d-CpGpAp(Me)TpCpG的两种光学纯非对映异构体。此外，还将描述一种制备尿苷-3',5'-环甲基膦酸酯的一锅法。我们还发现，RNA中的3',5'-甲基膦酸酯键对温和的酸处理不稳定。