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1
Synthesis of 3'-phosphates of diribonucleoside monophosphates via phosphotriester intermediates.通过磷酸三酯中间体合成二磷酸核苷单磷酸酯的3'-磷酸酯。
Nucleic Acids Res. 1976 Oct;3(10):2731-47. doi: 10.1093/nar/3.10.2731.
2
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.
3
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.
4
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.
5
Synthesis of oligonucleotides with sequences identical with or analogous to the 3'-end of 16S ribosomal RNA of Escherichia coli: preparation of m-6-2-A-C-C-U-C-C and A-C-C-U-C-m-4-2C via phosphotriester intermediates.合成与大肠杆菌16S核糖体RNA 3'-末端序列相同或相似的寡核苷酸：通过磷酸三酯中间体制备m-6-2-A-C-C-U-C-C和A-C-C-U-C-m-4-2C
Nucleic Acids Res. 1977 Mar;4(3):747-59. doi: 10.1093/nar/4.3.747.
6
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.
7
Nucleoside and deoxynucleoside phosphorylation in formamide solutions.甲酰胺溶液中的核苷和脱氧核苷磷酸化作用
Orig Life. 1982 Jun;12(2):143-51. doi: 10.1007/BF00927141.
8
The effect of Mg2+ and Ca2+ on urea-catalyzed phosphorylation reactions.
J Mol Evol. 1973 Nov 27;2(4):251-62. doi: 10.1007/BF01654094.
9
Synthesis of oligonucleotides with sequences identical with or analogous to the 3'-end of 16S ribosomal RNA of Escherichia coli: preparation of A-C-C-U-C-C via the modified phosphotriester method.合成与大肠杆菌16S核糖体RNA 3'-末端序列相同或相似的寡核苷酸：通过改良的磷酸三酯法制备A-C-C-U-C-C。
Nucleic Acids Res. 1977 Apr;4(4):1047-63. doi: 10.1093/nar/4.4.1047.
10
Formation of nucleoside 5'-polyphosphates under potentially prebiological conditions.在潜在的前生物条件下核苷5'-多磷酸的形成。
J Mol Evol. 1976 Oct 27;8(3):197-210. doi: 10.1007/BF01730997.

引用本文的文献

1
Universal solid supports for the synthesis of oligonucleotides with terminal 3'-phosphates.用于合成具有3'-磷酸末端的寡核苷酸的通用固相载体。
Nucleic Acids Res. 1989 Sep 25;17(18):7149-58. doi: 10.1093/nar/17.18.7149.
2
Nucleoside 3'-phosphotriesters as key intermediates for the oligoribonucleotide synthesis. IV. New method for removal of 2,2,2-trichloroethyl group and 31P NMR as a new tool for analysis of deblocking of internucleotide phosphate protecting groups.核苷3'-磷酸三酯作为寡核糖核苷酸合成的关键中间体。IV. 去除2,2,2-三氯乙基基团的新方法以及31P NMR作为分析核苷酸间磷酸保护基团脱保护的新工具。
Nucleic Acids Res. 1977 Jul;4(7):2321-9. doi: 10.1093/nar/4.7.2321.
3
Synthesis of oligonucleotides with sequences identical with or analogous to the 3'-end of 16S ribosomal RNA of Escherichia coli: preparation of A-C-C-U-C-C via the modified phosphotriester method.合成与大肠杆菌16S核糖体RNA 3'-末端序列相同或相似的寡核苷酸：通过改良的磷酸三酯法制备A-C-C-U-C-C。
Nucleic Acids Res. 1977 Apr;4(4):1047-63. doi: 10.1093/nar/4.4.1047.
4
Synthesis of oligonucleotides with sequences identical with or analogous to the 3'-end of 16S ribosomal RNA of Escherichia coli: preparation of m-6-2-A-C-C-U-C-C and A-C-C-U-C-m-4-2C via phosphotriester intermediates.合成与大肠杆菌16S核糖体RNA 3'-末端序列相同或相似的寡核苷酸：通过磷酸三酯中间体制备m-6-2-A-C-C-U-C-C和A-C-C-U-C-m-4-2C
Nucleic Acids Res. 1977 Mar;4(3):747-59. doi: 10.1093/nar/4.3.747.

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STUDIES ON POLYNUCLEOTIDES. XXXV. THE SPECIFIC SYNTHESIS OF C3'-C5'-LINKED RIBOOLIGONUCLEOTIDES. 8. THE SYNTHESIS OF RIBODINUCLEOTIDES BEARING 3'-PHOSPHOMONOESTER GROUPS.多核苷酸研究。XXXV. 3'-5'-连接的核糖寡核苷酸的特异性合成。8. 带有3'-磷酸单酯基团的核糖核苷酸的合成。
J Am Chem Soc. 1965 Jan 20;87:350-9. doi: 10.1021/ja01080a036.
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.
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[Synthesis of dinucleotides in the ribose series with terminal 3'-phosphate groups].[具有末端3'-磷酸基团的核糖系列二核苷酸的合成]
Justus Liebigs Ann Chem. 1967 Apr;703:215-24. doi: 10.1002/jlac.19677030125.
4
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.
5
The effective synthesis of uridylyl/3'-5'/5-methylcytidylyl/3'-5'/guanosine.尿苷酰基/3'-5'/5-甲基胞苷酰基/3'-5'/鸟苷的有效合成。
Nucleic Acids Res. 1976 Mar;3(3):709-20. doi: 10.1093/nar/3.3.709.
6
The synthesis of oligoribonucleotides. Part XI. Preparation of ribonucleoside 2'-acetal 3'-esters by selective deacylation.寡核糖核苷酸的合成。第十一章。通过选择性脱酰作用制备核糖核苷2'-缩醛3'-酯。
J Chem Soc Perkin 1. 1975(10):934-42. doi: 10.1039/p19750000934.
7
The modified nucleosides of tRNAs. II. Synthesis of 2'-O-methylcytidylyl (3'-5') cytidine.转运核糖核酸的修饰核苷。II. 2'-O-甲基胞苷酰（3'-5'）胞苷的合成。
Nucleic Acids Res. 1975 Jun;2(6):951-60. doi: 10.1093/nar/2.6.951.

通过磷酸三酯中间体合成二磷酸核苷单磷酸酯的3'-磷酸酯。

Synthesis of 3'-phosphates of diribonucleoside monophosphates via phosphotriester intermediates.

作者信息

van Boom J H, Burgers P M, Haasnoot C A

出版信息

Nucleic Acids Res. 1976 Oct;3(10):2731-47. doi: 10.1093/nar/3.10.2731.

DOI:10.1093/nar/3.10.2731
PMID:995650
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC343124/
Abstract

Phosphorylation of the easily accessible 3',5'-diesters 1a-d with diphenyl phosphorochloridate, followed by selective 5'-deacylation, affords the phosphotriester derivatives 2a-d in good yields. Alkaline treatment of 2a-d results in the formation of the 2',3'-cyclic phosphates (3a-d). The usefulness of the phosphotriester derivatives 2a-d is also demonstrated in the synthesis of the nucleotidyl-(3'-5')nucleoside 3'-phosphates U-Up (10a), U-Ap (11a), U-Cp (12a) and A-Gp (13a). The fully protected dinucleoside diphosphates 5c-8c, prepared by the phosphotriester method, are deprotected in two ways: (a) by a purely chemical method, affording the dinucleoside diphosphates in a circa one to one mixture of 2'- and 3'- isomers, 10b-13b and 10a-13a, respectively, and (b) by a mixed chemical-enzymatical approach which gives the pure 3'-phosphates (10a-13a).

摘要

用二苯基亚磷酰氯将易于获得的3',5'-二酯1a-d进行磷酸化，随后进行选择性5'-脱酰基反应，可高产率地得到磷酸三酯衍生物2a-d。对2a-d进行碱性处理会导致形成2',3'-环磷酸酯（3a-d）。磷酸三酯衍生物2a-d的实用性还体现在核苷酸基-(3'-5')核苷3'-磷酸酯U-Up（10a）、U-Ap（11a）、U-Cp（12a）和A-Gp（13a）的合成中。通过磷酸三酯法制备的完全保护的二核苷二磷酸酯5c-8c，有两种脱保护方法：（a）通过纯化学方法，分别得到2'-异构体和3'-异构体大约为1:1混合物的二核苷二磷酸酯，即10b-13b和10a-13a，以及（b）通过化学-酶混合方法，得到纯的3'-磷酸酯（10a-13a）。