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双二烷基氨基膦的原位活化——一种在聚合物载体上合成脱氧寡核苷酸的新方法。

In situ activation of bis-dialkylaminophosphines--a new method for synthesizing deoxyoligonucleotides on polymer supports.

作者信息

Barone A D, Tang J Y, Caruthers M H

出版信息

Nucleic Acids Res. 1984 May 25;12(10):4051-61. doi: 10.1093/nar/12.10.4051.

DOI:10.1093/nar/12.10.4051
PMID:6728676
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC318815/
Abstract

Deoxynucleoside phosphoramidites can be prepared in good yield from deoxynucleosides, bis- dialkylaminophosphines , and the corresponding dialkylamine hydrotetrazolide or tetrazole as catalysts. These phosphoramidites generated in situ lead to the direct synthesis of deoxyoligonucleotides on polymer supports.

摘要

脱氧核苷亚磷酰胺可以由脱氧核苷、双二烷基氨基膦以及相应的二烷基胺氢四唑化物或四唑作为催化剂以良好的产率制备。这些原位生成的亚磷酰胺可直接在聚合物载体上合成脱氧寡核苷酸。

相似文献

1
In situ activation of bis-dialkylaminophosphines--a new method for synthesizing deoxyoligonucleotides on polymer supports.双二烷基氨基膦的原位活化——一种在聚合物载体上合成脱氧寡核苷酸的新方法。
Nucleic Acids Res. 1984 May 25;12(10):4051-61. doi: 10.1093/nar/12.10.4051.
2
Application of 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite for in situ preparation of deoxyribonucleoside phosphoramidites and their use in polymer-supported synthesis of oligodeoxyribonucleotides.2-氰基乙基-N,N,N',N'-四异丙基亚磷酰胺在原位制备脱氧核糖核苷亚磷酰胺中的应用及其在聚合物支持的寡脱氧核苷酸合成中的用途。
Nucleic Acids Res. 1986 Sep 25;14(18):7391-403. doi: 10.1093/nar/14.18.7391.
3
Automatic synthesis of oligodeoxynucleotides and mixed oligodeoxynucleotides using the phosphoamidite method.使用亚磷酰胺法自动合成寡脱氧核苷酸和混合寡脱氧核苷酸。
Acta Chem Scand B. 1984;38(7):539-45. doi: 10.3891/acta.chem.scand.38b-0539.
4
Polymer support oligonucleotide synthesis XVIII: use of beta-cyanoethyl-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product.聚合物载体寡核苷酸合成 XVIII：脱氧核苷的β-氰基乙基-N，N-二烷基氨基-/N-吗啉代亚磷酰胺用于 DNA 片段合成，简化最终产物的脱保护和分离
Nucleic Acids Res. 1984 Jun 11;12(11):4539-57. doi: 10.1093/nar/12.11.4539.
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Solid-phase synthesis of polynucleotides: V. Synthesis of oligodeoxyribonucleotides by the phosphomonotriazolide method.多核苷酸的固相合成：V. 用磷酸单三唑酯法合成寡脱氧核糖核苷酸
Nucleic Acids Symp Ser. 1980(7):281-91.
6
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.
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Development in the phosphite-triester method of synthesis of oligonucleotides.亚磷酸三酯法合成寡核苷酸的进展。
Nucleic Acids Symp Ser. 1980(7):133-45.
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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
The phosphorothioite method. Synthesis of deoxyoligonucleotides on polymer supports by using nucleoside phosphorothioites.
Nucleic Acids Symp Ser. 1986(17):77-80.
10
Simple and rapid procedure for synthesis of deoxynucleoside 3'-2-cyanoethyl-N,N-diisopropyl-amino phosphites.合成脱氧核苷3'-2-氰基乙基-N，N-二异丙基亚磷酰胺的简单快速方法。
Nucleic Acids Symp Ser. 1987(18):177-80.

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本文引用的文献

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Synthesis of oligodeoxyribonucleotides on silica gel support.硅胶载体上寡脱氧核糖核苷酸的合成。
Nucleic Acids Res. 1981 Jun 25;9(12):2807-17. doi: 10.1093/nar/9.12.2807.
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Restriction and modification of a self-complementary octanucleotide containing the EcoRI substrate.
J Mol Biol. 1975 Dec 5;99(2):237-61. doi: 10.1016/s0022-2836(75)80143-4.
Nucleic Acids Res. 2018 Sep 19;46(16):8069-8078. doi: 10.1093/nar/gky669.
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Discovery of inhibitors of Leishmania β-1,2-mannosyltransferases using a click-chemistry-derived guanosine monophosphate library.利用点击化学衍生的鸟苷一磷酸文库发现利什曼原虫β-1,2-甘露糖基转移酶抑制剂。
PLoS One. 2012;7(2):e32642. doi: 10.1371/journal.pone.0032642. Epub 2012 Feb 29.
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High relaxivity magnetic resonance imaging contrast agents. Part 1. Impact of single donor atom substitution on relaxivity of serum albumin-bound gadolinium complexes.高弛豫磁共振成像对比剂。第 1 部分。单供体原子取代对血清白蛋白结合钆配合物弛豫率的影响。
Invest Radiol. 2010 Oct;45(10):600-12. doi: 10.1097/RLI.0b013e3181ee5a9e.
6
The synthesis and stability of oligodeoxyribonucleotides containing the deoxyadenosine mimic 1-(2'-deoxy-beta-D-ribofuranosyl)imidazole-4-carboxamide.含有脱氧腺苷类似物1-(2'-脱氧-β-D-呋喃核糖基)咪唑-4-甲酰胺的寡脱氧核糖核苷酸的合成与稳定性
Nucleic Acids Res. 1997 Feb 1;25(3):559-67. doi: 10.1093/nar/25.3.559.
7
Preparation of oligoribonucleotides containing 4-thiouridine using Fpmp chemistry. Photo-crosslinking to RNA binding proteins using 350 nm irradiation.使用Fpmp化学方法制备含4-硫尿苷的寡核糖核苷酸。利用350纳米辐射对RNA结合蛋白进行光交联。
Nucleic Acids Res. 1996 Aug 15;24(16):3173-80. doi: 10.1093/nar/24.16.3173.
8
The cysteine conserved among DNA cytosine methylases is required for methyl transfer, but not for specific DNA binding.DNA胞嘧啶甲基转移酶中保守的半胱氨酸是甲基转移所必需的，但不是特异性DNA结合所必需的。
Nucleic Acids Res. 1993 Jan 25;21(2):295-301. doi: 10.1093/nar/21.2.295.
9
Modulation of oligonucleotide duplex and triplex stability via hydrophobic interactions.通过疏水相互作用调节寡核苷酸双链体和三链体的稳定性。
Nucleic Acids Res. 1993 Dec 25;21(25):5909-15. doi: 10.1093/nar/21.25.5909.
10
Strings of contiguous modified pentanucleotides with increased DNA-binding affinity can be used for DNA sequencing by primer walking.具有增强的DNA结合亲和力的连续修饰五核苷酸串可用于通过引物步移进行DNA测序。
Proc Natl Acad Sci U S A. 1993 Dec 15;90(24):11460-2. doi: 10.1073/pnas.90.24.11460.