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新型催化磷酸保护基团在高效磷酸三酯寡核苷酸合成中的应用。

Application of new catalytic phosphate protecting groups for the highly efficient phosphotriester oligonucleotide synthesis.

作者信息

Efimov V A, Buryakova A A, Dubey I Y, Polushin N N, Chakhmakhcheva O G

出版信息

Nucleic Acids Res. 1986 Aug 26;14(16):6525-40. doi: 10.1093/nar/14.16.6525.

DOI:10.1093/nar/14.16.6525
PMID:3748819
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC311661/
Abstract

An effective procedure for the synthesis of oligonucleotides by the phosphotriester method has been developed. The procedure is based on the use of phosphate protecting groups enabling O-nucleophilic intramolecular catalysis in the reaction of internucleotide bond formation under the action of arylsulfonyl chlorides and their derivatives. Using this new procedure, the time needed to perform one elongation step on polymer support is 7-8 min. The effectiveness of the methodology has been demonstrated in the synthesis of many oligodeoxyribonucleotides of different length with high yields.

摘要

已开发出一种通过磷酸三酯法合成寡核苷酸的有效方法。该方法基于使用磷酸保护基团,在芳基磺酰氯及其衍生物的作用下,在核苷酸间键形成反应中实现O-亲核分子内催化。使用这种新方法,在聚合物载体上进行一个延伸步骤所需的时间为7-8分钟。该方法的有效性已在合成许多不同长度的寡脱氧核糖核苷酸中得到证明,且产率很高。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/33ba/311661/7e69337833e6/nar00285-0197-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/33ba/311661/ad66c81b158d/nar00285-0196-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/33ba/311661/7e69337833e6/nar00285-0197-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/33ba/311661/ad66c81b158d/nar00285-0196-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/33ba/311661/7e69337833e6/nar00285-0197-a.jpg

相似文献

1
Application of new catalytic phosphate protecting groups for the highly efficient phosphotriester oligonucleotide synthesis.新型催化磷酸保护基团在高效磷酸三酯寡核苷酸合成中的应用。
Nucleic Acids Res. 1986 Aug 26;14(16):6525-40. doi: 10.1093/nar/14.16.6525.
2
Rapid synthesis of oligonucleotides by the phosphotriester method.用磷酸三酯法快速合成寡核苷酸。
Biochimie. 1985 Jul-Aug;67(7-8):791-5. doi: 10.1016/s0300-9084(85)80169-3.
3
Silica gel: an improved support for the solid-phase phosphotriester synthesis of oligonucleotides.硅胶:用于寡核苷酸固相磷酸三酯合成的一种改进载体。
Nucleic Acids Res. 1982 Nov 25;10(22):7439-48. doi: 10.1093/nar/10.22.7439.
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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.
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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.
6
Highly efficient oligodeoxyribonucleotide synthesis using fully base protected phosphodiester building blocks carrying 2-(1-methylimidazol-2-yl) phenyl protection of the phosphate.使用携带磷酸基团2-(1-甲基咪唑-2-基)苯基保护的全碱基保护的磷酸二酯构建块进行高效的寡脱氧核糖核苷酸合成。
Nucleic Acids Res. 1986 Feb 25;14(4):1811-24. doi: 10.1093/nar/14.4.1811.
7
Rapid synthesis of oligodeoxyribonucleotides VI. Efficient, mechanised synthesis of heptadecadeoxyribonucleotides by an improved solid phase phosphotriester route.寡脱氧核糖核苷酸的快速合成VI。通过改进的固相磷三酯路线高效、机械化合成十七聚脱氧核糖核苷酸。
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Rapid synthesis of oligodeoxyribonucleotides. VII. Solid phase synthesis of oligodeoxyribonucleotides by a continuous flow phosphotriester method on a kieselguhr-polyamide support.寡脱氧核糖核苷酸的快速合成。VII. 在硅藻土-聚酰胺载体上通过连续流动磷酸三酯法固相合成寡脱氧核糖核苷酸。
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Solid phase synthesis of polynucleotides. VIII. Synthesis of mixed oligodeoxyribonucleotides by the phosphotriester solid phase method.多核苷酸的固相合成。VIII. 用磷酸三酯固相法合成混合寡脱氧核糖核苷酸。
Nucleic Acids Res. 1983 Jan 25;11(2):477-88. doi: 10.1093/nar/11.2.477.
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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.

引用本文的文献

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2
Alternative synthetic tools to phospho-specific antibodies for phosphoproteome analysis: progress and prospects.用于磷酸化蛋白质组分析的磷酸特异性抗体的替代合成工具:进展与展望
J Chem Biol. 2013 Jul 9;6(4):175-84. doi: 10.1007/s12154-013-0100-y.
3
Synthesis and evaluation of some properties of chimeric oligomers containing PNA and phosphono-PNA residues.

本文引用的文献

1
Simultaneous rapid chemical synthesis of over one hundred oligonucleotides on a microscale.在微尺度上同时快速化学合成超过一百个寡核苷酸。
EMBO J. 1984 Apr;3(4):801-5. doi: 10.1002/j.1460-2075.1984.tb01888.x.
2
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.
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Rapid synthesis of long-chain deoxyribooligonucleotides by the N-methylimidazolide phosphotriester method.
含肽核酸(PNA)和膦酰基 - 肽核酸残基的嵌合寡聚物的合成及某些性质的评估
Nucleic Acids Res. 1998 Jan 15;26(2):566-75. doi: 10.1093/nar/26.2.566.
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A new approach to the synthesis of the 5'-deoxy-5'-methylphosphonate linked thymidine oligonucleotide analogues.一种合成5'-脱氧-5'-甲基膦酸酯连接的胸腺嘧啶寡核苷酸类似物的新方法。
Nucleic Acids Res. 1995 Mar 25;23(6):893-900. doi: 10.1093/nar/23.6.893.
通过N-甲基咪唑啉磷酸三酯法快速合成长链脱氧核糖寡核苷酸。
Nucleic Acids Res. 1983 Dec 10;11(23):8369-87. doi: 10.1093/nar/11.23.8369.
4
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.
5
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.
6
Highly efficient oligodeoxyribonucleotide synthesis using fully base protected phosphodiester building blocks carrying 2-(1-methylimidazol-2-yl) phenyl protection of the phosphate.使用携带磷酸基团2-(1-甲基咪唑-2-基)苯基保护的全碱基保护的磷酸二酯构建块进行高效的寡脱氧核糖核苷酸合成。
Nucleic Acids Res. 1986 Feb 25;14(4):1811-24. doi: 10.1093/nar/14.4.1811.