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作为多核苷酸合成关键中间体的受保护脱氧核糖核苷-3'-芳基磷酸二酯。构建与劳氏肉瘤病毒35S RNA末端序列类似的二十核苷酸。

Protected deoxyribonucleoside-3' aryl phosphodiesters as key intermediates in polynucleotide synthesis. Construction of an icosanucleotide analogous to the sequence at the ends of Rous sarcoma virus 35S RNA.

作者信息

Gough G R, Singleton C K, Weith H L, Gilham P T

出版信息

Nucleic Acids Res. 1979 Apr;6(4):1557-70. doi: 10.1093/nar/6.4.1557.

DOI:10.1093/nar/6.4.1557
PMID:221888
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC327790/
Abstract

Several modifications have been incorporated into the phosphotriester strategy for chemical synthesis of oligodeoxyribonucleotides. These include high-yield methods of preparation and isolation of O5', N-protected deoxyribonucleoside-3' p-chlorophenyl phosphates which serve as key intermediates, and the elimination of some superfluous manipulation and purification steps commonly used in the process of synthesizing oligonucleotide blocks. In addition, two new arylsulfonyl nitroimidazole derivatives have been prepared and found to be highly effective agents for internucleotide bond formation. These techniques have been applied in construction of the iconsamer d(G-C-C-A-T-T-T-T-A-C-C-A-T-T-C-A-C-C-A)-rC, equivalent to a ribonucleotide sequence located at both the 5' and 3' ends of Rous sarcoma virus 35S RNA.

摘要

在化学合成寡脱氧核糖核苷酸的磷酸三酯策略中已经纳入了若干改进。这些改进包括作为关键中间体的O5'，N-保护的脱氧核糖核苷-3'-对氯苯基磷酸酯的高产率制备和分离方法，以及消除了寡核苷酸片段合成过程中通常使用的一些多余操作和纯化步骤。此外，还制备了两种新的芳基磺酰基硝基咪唑衍生物，发现它们是用于核苷酸间键形成的高效试剂。这些技术已应用于同聚物d(G-C-C-A-T-T-T-T-A-C-C-A-T-T-C-A-C-C-A)-rC的构建，该同聚物等同于劳斯肉瘤病毒35S RNA 5'和3'末端的核糖核苷酸序列。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/196c/327790/68ad40717951/nar00445-0342-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/196c/327790/68ad40717951/nar00445-0342-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/196c/327790/68ad40717951/nar00445-0342-a.jpg

相似文献

1
Protected deoxyribonucleoside-3' aryl phosphodiesters as key intermediates in polynucleotide synthesis. Construction of an icosanucleotide analogous to the sequence at the ends of Rous sarcoma virus 35S RNA.作为多核苷酸合成关键中间体的受保护脱氧核糖核苷-3'-芳基磷酸二酯。构建与劳氏肉瘤病毒35S RNA末端序列类似的二十核苷酸。
Nucleic Acids Res. 1979 Apr;6(4):1557-70. doi: 10.1093/nar/6.4.1557.
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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。
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引用本文的文献

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Some observations relating to the oximate ion promoted unblocking of oligonucleotide aryl esters.

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
CV. Total synthesis of the structural gene for an alanine transfer ribonucleic acid from yeast. Chemical synthesis of an icosadeoxyribonucleotide corresponding to the nucleotide sequence 31 to 50.简历。酵母丙氨酸转移核糖核酸结构基因的全合成。对应于核苷酸序列31至50的二十碳脱氧核糖核苷酸的化学合成。
J Mol Biol. 1972 Dec 28;72(2):251-88. doi: 10.1016/0022-2836(72)90148-9.
3
Separation of oligonucleotides, nucleotides, and nucleosides on columns of polystyrene anion-exchangers with solvent systems containing ethanol.
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.
4
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.
5
Studies on transfer ribonucleic acids and related compounds. XL. Synthesis of an eicosaribonucleotide corresponding to residues 35-54 of tRNAfMet from E. coli.转移核糖核酸及相关化合物的研究。XL。对应于大肠杆菌甲硫氨酸起始转运核糖核酸（tRNAfMet）35 - 54位残基的二十碳核糖核苷酸的合成。
Nucleic Acids Res. 1981 Jul 24;9(14):3503-22. doi: 10.1093/nar/9.14.3503.
6
Synthesis of the human insulin gene. Part III. Chemical synthesis of 5'-phosphomonoester group containing deoxyribooligonucleotides by the modified phosphotriester method. Its application in the synthesis of seventeen fragments constituting human insulin C-chain DNA.人胰岛素基因的合成。第三部分。用改进的磷酸三酯法化学合成含5'-磷酸单酯基团的脱氧核糖寡核苷酸。其在构成人胰岛素C链DNA的17个片段合成中的应用。
Nucleic Acids Res. 1980 Dec 11;8(23):5753-65. doi: 10.1093/nar/8.23.5753.
7
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Nucleic Acids Res. 1982 Aug 11;10(15):4467-82. doi: 10.1093/nar/10.15.4467.
8
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Nucleic Acids Res. 1980 May 10;8(9):2039-53. doi: 10.1093/nar/8.9.2039.
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10
Sequence analysis of a cDNA coding for a pancreatic precursor to somatostatin.编码生长抑素胰腺前体的cDNA的序列分析。
Proc Natl Acad Sci U S A. 1981 Nov;78(11):6694-8. doi: 10.1073/pnas.78.11.6694.
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4
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Eur J Biochem. 1975 Oct 15;58(2):383-95. doi: 10.1111/j.1432-1033.1975.tb02385.x.
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6
The use of terminal blocking groups for the specific joining of oligonucleotides in RNA ligase reactions containing equimolar concentrations of acceptor and donor molecules.在含有等摩尔浓度受体和供体分子的RNA连接酶反应中，使用末端封闭基团实现寡核苷酸的特异性连接。
Nucleic Acids Res. 1976 Nov;3(11):3157-66. doi: 10.1093/nar/3.11.3157.
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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。
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J Chromatogr. 1977 Jun 1;136(1):159-61. doi: 10.1016/s0021-9673(00)83005-8.
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Expression in Escherichia coli of a chemically synthesized gene for the hormone somatostatin.生长抑素激素化学合成基因在大肠杆菌中的表达。
Science. 1977 Dec 9;198(4321):1056-63. doi: 10.1126/science.412251.
10
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.