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1
A study of the efficiency and the problem of sulfonation of several condensing reagents and their mechanisms for the chemical synthesis of deoxyoligoribonucleotides.几种缩合试剂磺化用于化学合成脱氧寡核糖核苷酸的效率、问题及其机制的研究
Nucleic Acids Res. 1980 Nov 25;8(22):5445-59. doi: 10.1093/nar/8.22.5445.
2
Arylsulfonyltetrazoles, new coupling reagents and further improvements in the triester method for the synthesis of deoxyribooligonucleotides.芳基磺酰四唑，新型偶联试剂以及脱氧核糖寡核苷酸合成三酯法的进一步改进。
Nucleic Acids Res. 1977 Feb;4(2):353-71. doi: 10.1093/nar/4.2.353.
3
A rapid internucleotide bond formation for the phosphotriester approach by use of new condensing reagents.通过使用新型缩合试剂，磷酸三酯法实现核苷酸间快速成键。
Nucleic Acids Symp Ser. 1984(15):93-6.
4
Mechanistic studies on the phosphoramidite coupling reaction in oligonucleotide synthesis. I. Evidence for nucleophilic catalysis by tetrazole and rate variations with the phosphorus substituents.寡核苷酸合成中磷酰胺酯偶联反应的机理研究。I. 四唑亲核催化的证据以及磷取代基对反应速率的影响
Nucleic Acids Res. 1987 Feb 25;15(4):1729-43. doi: 10.1093/nar/15.4.1729.
5
The case of sulfonation in the chemical synthesis of oligonucleotides.寡核苷酸化学合成中的磺化反应实例。
Nucleic Acids Res. 1980 May 24;8(10):2301-5. doi: 10.1093/nar/8.10.2301.
6
Simplications in the synthesis of short oligonucleotide blocks.短寡核苷酸片段合成中的简化方法。
Nucleic Acids Res. 1980 Nov 25;8(22):5461-71. doi: 10.1093/nar/8.22.5461.
7
Synthesis of oligodeoxyribonucleotides by solid phase phosphotriester method on a reduced scale; preparation of oligonucleotides for improved promoter sequence.在小规模下通过固相磷三酯法合成寡脱氧核糖核苷酸；制备用于改进启动子序列的寡核苷酸。
Nucleic Acids Symp Ser. 1982(11):77-80.
8
A novel class of condensing reagents in phosphodiester oligodeoxyribonucleotides synthesis. Application of the constituents of free terminal carboxy oxytocine gene.磷酸二酯寡脱氧核糖核苷酸合成中的一类新型缩合试剂。游离末端羧基催产素基因成分的应用。
Nucleic Acids Symp Ser. 1980(7):23-37.
9
Synthesis and reactions of a nucleoside derivative of phosphoric sulfonic anhydride. Studies related to the mechanisms of coupling reactions in the chemical synthesis of oligodeoxyribonucleotides by phosphotriester procedures.磷磺酸酐核苷衍生物的合成与反应。与通过磷酸三酯法化学合成寡脱氧核糖核苷酸中偶联反应机制相关的研究。
Nucleic Acids Res. 1984 Dec 11;12(23):9123-35. doi: 10.1093/nar/12.23.9123.
10
Improvements to solid phase phosphotriester synthesis of deoxyoligonucleotides.脱氧寡核苷酸固相磷三酯合成法的改进
Nucleic Acids Res. 1982 Sep 25;10(18):5605-20. doi: 10.1093/nar/10.18.5605.

引用本文的文献

1
New effective method for the synthesis of oligonucleotides via phosphotriester intermediates.通过磷酸三酯中间体合成寡核苷酸的新有效方法。
Nucleic Acids Res. 1982 Nov 11;10(21):6675-94. doi: 10.1093/nar/10.21.6675.
2
Recent developments in the chemical synthesis of polynucleotides.多核苷酸化学合成的最新进展。
Nucleic Acids Res. 1982 Nov 11;10(21):6553-70. doi: 10.1093/nar/10.21.6553.
3
General scheme of the phosphotriester condensation in the oligodeoxyribonucleotide synthesis with arylsulfonyl chlorides and arylsulfonyl azolides.在使用芳基磺酰氯和芳基磺酰叠氮化物进行寡脱氧核糖核苷酸合成中磷酸三酯缩合的一般方案。
Nucleic Acids Res. 1984 Feb 24;12(4):2091-110. doi: 10.1093/nar/12.4.2091.
4
Synthesis and reactions of a nucleoside derivative of phosphoric sulfonic anhydride. Studies related to the mechanisms of coupling reactions in the chemical synthesis of oligodeoxyribonucleotides by phosphotriester procedures.磷磺酸酐核苷衍生物的合成与反应。与通过磷酸三酯法化学合成寡脱氧核糖核苷酸中偶联反应机制相关的研究。
Nucleic Acids Res. 1984 Dec 11;12(23):9123-35. doi: 10.1093/nar/12.23.9123.
5
The kinetics of phosphotriester condensation reactions on solid support.固相载体上磷酸三酯缩合反应的动力学
Nucleic Acids Res. 1984 Aug 24;12(16):6511-22. doi: 10.1093/nar/12.16.6511.
6
Fluorescent labelling of tRNA and oligodeoxynucleotides using T4 RNA ligase.使用T4 RNA连接酶对tRNA和寡脱氧核苷酸进行荧光标记。
Nucleic Acids Res. 1984 Feb 24;12(4):1791-810. doi: 10.1093/nar/12.4.1791.
7
Gene expression: chemical synthesis of E. coli ribosome binding sites and their use in directing the expression of mammalian proteins in bacteria.基因表达：大肠杆菌核糖体结合位点的化学合成及其在指导细菌中哺乳动物蛋白表达中的应用。
Nucleic Acids Res. 1982 Oct 25;10(20):6319-29. doi: 10.1093/nar/10.20.6319.
8
Construction of a general vector for efficient expression of mammalian proteins in bacteria: use of a synthetic ribosome binding site.用于在细菌中高效表达哺乳动物蛋白的通用载体构建：合成核糖体结合位点的应用。
Proc Natl Acad Sci U S A. 1981 Sep;78(9):5543-8. doi: 10.1073/pnas.78.9.5543.
9
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.
10
Improved rapid phosphotriester synthesis of oligodeoxyribonucleotides using oxygen-nucleophilic catalysts.使用氧亲核催化剂改进寡脱氧核糖核苷酸的快速磷酸三酯合成法。
Nucleic Acids Res. 1985 May 24;13(10):3651-66. doi: 10.1093/nar/13.10.3651.

本文引用的文献

1
The case of sulfonation in the chemical synthesis of oligonucleotides.寡核苷酸化学合成中的磺化反应实例。
Nucleic Acids Res. 1980 May 24;8(10):2301-5. doi: 10.1093/nar/8.10.2301.
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
Total synthesis of the gene for an alanine transfer ribonucleic acid from yeast.酵母丙氨酸转移核糖核酸基因的全合成
Nature. 1970 Jul 4;227(5253):27-34. doi: 10.1038/227027a0.
4
A rapid and convenient synthesis of poly-thymidylic acid by the modified triester approach.通过改进的三酯法快速便捷地合成聚胸腺嘧啶核苷酸。
Nucleic Acids Res. 1977 Aug;4(8):2757-65. doi: 10.1093/nar/4.8.2757.
5
Total synthesis of the structural gene for the precursor of a tyrosine suppressor transfer RNA from Escherichia coli. 1. General introduction.大肠杆菌酪氨酸抑制性转移核糖核酸前体结构基因的全合成。1. 概述。
J Biol Chem. 1976 Feb 10;251(3):565-70.
6
A synthetic tyrosine suppressor tRNA gene with an altered promoter sequence. Its cloning and relative expression in vivo.一个具有改变启动子序列的合成酪氨酸抑制tRNA基因。其克隆及在体内的相对表达。
J Biol Chem. 1979 Nov 10;254(21):10803-10.
7
Synthesis of the human insulin gene. Part II. Further improvements in the modified phosphotriester method and the synthesis of seventeen deoxyribooligonucleotide fragments constituting human insulin chains B and mini-CDNA.人胰岛素基因的合成。第二部分。改良磷酸三酯法的进一步改进以及构成人胰岛素B链和微型cDNA的17个脱氧核糖寡核苷酸片段的合成。
Nucleic Acids Res. 1979 Dec 20;7(8):2199-212. doi: 10.1093/nar/7.8.2199.
8
Arylsulfonyltetrazoles, new coupling reagents and further improvements in the triester method for the synthesis of deoxyribooligonucleotides.芳基磺酰四唑，新型偶联试剂以及脱氧核糖寡核苷酸合成三酯法的进一步改进。
Nucleic Acids Res. 1977 Feb;4(2):353-71. doi: 10.1093/nar/4.2.353.
9
The use of arylsulfonyltriazoles for the synthesis of oligonucleotides by the triester approach.
J Am Chem Soc. 1975 Dec 10;97(25):7332-7. doi: 10.1021/ja00858a021.
10
Chemical synthesis and sequence studies of deoxyribooligonucleotides which constitute the duplex sequence of the lactose operator of Escherichia coli.构成大肠杆菌乳糖操纵基因双链序列的脱氧核糖寡核苷酸的化学合成及序列研究。
J Biol Chem. 1975 Jun 25;250(12):4592-600.

几种缩合试剂磺化用于化学合成脱氧寡核糖核苷酸的效率、问题及其机制的研究

A study of the efficiency and the problem of sulfonation of several condensing reagents and their mechanisms for the chemical synthesis of deoxyoligoribonucleotides.

作者信息

Seth A K, Jay E

出版信息

Nucleic Acids Res. 1980 Nov 25;8(22):5445-59. doi: 10.1093/nar/8.22.5445.

DOI:10.1093/nar/8.22.5445
PMID:6894029
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC324313/
Abstract

The efficiencies and problems of sulfonation of several condensing reagents for deoxyoligoribonucleotide synthesis have been studied. While 2,4,6-triisopropylbenzenesulfonyl chloride (TPSC1) gave very low yield and slow rate of coupling, the new 1:3 mixture of TPSC1 and tetrazole afforded excellent yield and extremely fast rate of reaction with the lowest rate of sulfonation. The difference and advantages of this mixture over triisopropylbenzenesulfonyl tetrazole (TPSTe) and mesitylenesulfonyl tetrazole (MSTe) are discussed. Mechanisms for the coupling reactions with these condensing reagents to account for the difference in their rates and yields of coupling are discussed.

摘要

研究了几种用于脱氧寡核糖核苷酸合成的缩合试剂磺化反应的效率和问题。虽然2,4,6-三异丙基苯磺酰氯（TPSC1）的产率很低且偶联速率很慢，但新的TPSC1与四氮唑1:3混合物的产率极高，反应速率极快，磺化速率最低。讨论了该混合物相对于三异丙基苯磺酰四氮唑（TPSTe）和均三甲苯磺酰四氮唑（MSTe）的差异和优势。讨论了与这些缩合试剂进行偶联反应的机理，以解释它们偶联速率和产率的差异。