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用于合成寡脱氧核糖核苷酸的亚磷酰胺方法的改进。

Improvements in the phosphoramidite procedure for the synthesis of oligodeoxyribonucleotides.

作者信息

Dörper T, Winnacker E L

出版信息

Nucleic Acids Res. 1983 May 11;11(9):2575-84. doi: 10.1093/nar/11.9.2575.

DOI:10.1093/nar/11.9.2575
PMID:6856470
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC325909/
Abstract

The paper describes an improved method for the synthesis of oligodeoxyribonucleotides using phosphoramidite chemistry. Our procedure relies on novel phosphoramidite intermediates, the deoxyribonucleoside-3'-morpholine-methoxyphosphins. These compounds are extremely stable and can be purified readily. Condensation reactions during solid-phase synthesis can thus be performed with high efficiency and result in a high yield synthesis of long chain oligodeoxyribonucleotides.

摘要

本文描述了一种使用亚磷酰胺化学合成寡脱氧核糖核苷酸的改进方法。我们的方法依赖于新型亚磷酰胺中间体,即脱氧核糖核苷-3'-吗啉甲氧基膦。这些化合物极其稳定,易于纯化。因此,固相合成过程中的缩合反应可以高效进行,并能高产率合成长链寡脱氧核糖核苷酸。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f7e/325909/a63040a7ed16/nar00354-0078-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f7e/325909/fb6926712c08/nar00354-0075-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f7e/325909/a63040a7ed16/nar00354-0078-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f7e/325909/fb6926712c08/nar00354-0075-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4f7e/325909/a63040a7ed16/nar00354-0078-a.jpg

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Improvements in the phosphoramidite procedure for the synthesis of oligodeoxyribonucleotides.用于合成寡脱氧核糖核苷酸的亚磷酰胺方法的改进。
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本文引用的文献

1
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.
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Sequencing end-labeled DNA with base-specific chemical cleavages.通过碱基特异性化学切割对末端标记的DNA进行测序。
Methods Enzymol. 1980;65(1):499-560. doi: 10.1016/s0076-6879(80)65059-9.
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Synthesis of thymidine oligonucleotides by phosphite triester intermediates.
滤膜支持的亚磷酸酯法寡核苷酸合成。
Nucleic Acids Res. 1984 Dec 11;12(23):9137-42. doi: 10.1093/nar/12.23.9137.
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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
Chemical synthesis of oligonucleotides containing a free sulphydryl group and subsequent attachment of thiol specific probes.含有游离巯基的寡核苷酸的化学合成及硫醇特异性探针的后续连接。
Nucleic Acids Res. 1985 Jun 25;13(12):4485-502. doi: 10.1093/nar/13.12.4485.
6
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.
7
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.
8
Solid phase synthesis of oligoribonucleotides using o-nitrobenzyl protection of 2'-hydroxyl via a phosphite triester approach.通过亚磷酸三酯法利用邻硝基苄基对2'-羟基进行保护的寡核糖核苷酸的固相合成。
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9
A sensitive and rapid gel retention assay for nuclear factor I and other DNA-binding proteins in crude nuclear extracts.一种用于检测粗核提取物中核因子I和其他DNA结合蛋白的灵敏且快速的凝胶滞留分析方法。
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Synthesis of a trans-syn thymine dimer building block. Solid phase synthesis of CGTAT[t,s]TATGC.反式-顺式胸腺嘧啶二聚体构建模块的合成。CGTAT[t,s]TATGC的固相合成。
Nucleic Acids Res. 1988 Jun 10;16(11):5123-36. doi: 10.1093/nar/16.11.5123.
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J Am Chem Soc. 1976 Jun 9;98(12):3655-61. doi: 10.1021/ja00428a045.
4
Synthesis of oligoribonucleotides based on the facile cleavage of methyl phosphotriester intermediates.基于甲基磷酸三酯中间体的简便裂解合成寡核糖核苷酸。
J Am Chem Soc. 1977 May 11;99(10):3526-8. doi: 10.1021/ja00452a069.