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使用1-[(2-氯-4-甲基)苯基]-4-甲氧基哌啶-4-基（Ctmp）基团保护2'-羟基官能团并采用H-膦酸酯法进行寡核糖核苷酸的固相合成。

Solid phase synthesis of oligoribonucleotides using the 1-[(2-chloro-4-methyl)phenyl]-4-methoxypiperidin-4-yl (Ctmp) group for the protection of the 2'-hydroxy functions and the H-phosphonate approach.

作者信息

Sakatsume O, Ohtsuki M, Takaku H, Reese C B

机构信息

Department of Industrial Chemistry, Chiba Institute of Technology, Japan.

出版信息

Nucleic Acids Res. 1989 May 25;17(10):3689-97. doi: 10.1093/nar/17.10.3689.

DOI:10.1093/nar/17.10.3689
PMID:2734100
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC317850/
Abstract

The solid phase synthesis of oligoribonucleotides using the H-phosphonate approach and the 1-[(2-chloro-4-methyl)phenyl]-4-methoxypiperidin-4-yl (Ctmp) and dimethoxytrityl (DMTr) groups, respectively, for the protection of the 2'- and 5'-hydroxy functions is described. The use of a new reagent, tris-(1,1,1,3,3,3-hexafluoro-2-propyl) phosphite for the preparation of nucleoside H-phosphonate units is also discussed in detail.

摘要

描述了使用H-膦酸酯方法以及分别使用1-[(2-氯-4-甲基)苯基]-4-甲氧基哌啶-4-基（Ctmp）和二甲氧基三苯甲基（DMTr）基团对2'-和5'-羟基官能团进行保护来固相合成寡核糖核苷酸。还详细讨论了使用一种新试剂亚磷酸三（1,1,1,3,3,3-六氟-2-丙基）酯来制备核苷H-膦酸酯单元。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab12/317850/325ee8ccefd0/nar00127-0070-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab12/317850/325ee8ccefd0/nar00127-0070-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ab12/317850/325ee8ccefd0/nar00127-0070-a.jpg

相似文献

1
Solid phase synthesis of oligoribonucleotides using the 1-[(2-chloro-4-methyl)phenyl]-4-methoxypiperidin-4-yl (Ctmp) group for the protection of the 2'-hydroxy functions and the H-phosphonate approach.使用1-[(2-氯-4-甲基)苯基]-4-甲氧基哌啶-4-基（Ctmp）基团保护2'-羟基官能团并采用H-膦酸酯法进行寡核糖核苷酸的固相合成。
Nucleic Acids Res. 1989 May 25;17(10):3689-97. doi: 10.1093/nar/17.10.3689.
2
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引用本文的文献

1
Evaluation of 2'-hydroxyl protection in RNA-synthesis using the H-phosphonate approach.使用H-膦酸酯法评估RNA合成中2'-羟基的保护作用。
Nucleic Acids Res. 1994 Jan 11;22(1):94-9. doi: 10.1093/nar/22.1.94.
2
Use of the 1-(2-fluorophenyl)-4-methoxypiperidin-4-yl (Fpmp) and related protecting groups in oligoribonucleotide synthesis: stability of internucleotide linkages to aqueous acid.1-(2-氟苯基)-4-甲氧基哌啶-4-基（Fpmp）及相关保护基团在寡核糖核苷酸合成中的应用：核苷酸间连接对酸水溶液的稳定性
Nucleic Acids Res. 1994 Jun 25;22(12):2209-16. doi: 10.1093/nar/22.12.2209.
3
Synthesis and applications of oligoribonucleotides with selected 2'-O-methylation using the 2'-O-[1-(2-fluorophenyl)-4-methoxypiperidin-4-yl] protecting group.

本文引用的文献

1
Translational initiation in prokaryotes.原核生物中的翻译起始
Annu Rev Microbiol. 1981;35:365-403. doi: 10.1146/annurev.mi.35.100181.002053.
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Localization of Q-beta maturation cistron ribosome binding site.Q-β成熟顺反子核糖体结合位点的定位
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使用2'-O-[1-(2-氟苯基)-4-甲氧基哌啶-4-基]保护基团合成及应用具有特定2'-O-甲基化的寡核糖核苷酸
Nucleic Acids Res. 1990 Sep 11;18(17):5143-51. doi: 10.1093/nar/18.17.5143.
4
Use of new phosphonylating and coupling agents in the synthesis of oligodeoxyribonucleotides via the H-phosphonate approach.新型膦酰化和偶联剂在通过H-膦酸酯法合成寡脱氧核糖核苷酸中的应用。
Nucleic Acids Res. 1990 Jun 11;18(11):3327-31. doi: 10.1093/nar/18.11.3327.
5
A convenient approach to the synthesis of medium size oligodeoxyribonucleotides by improved new phosphite method.一种通过改进的新亚磷酸酯法合成中等长度寡脱氧核糖核苷酸的简便方法。
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4
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。
Nucleic Acids Res. 1986 Aug 11;14(15):6265-79. doi: 10.1093/nar/14.15.6265.
5
Synthesis of DNA via deoxynucleoside H-phosphonate intermediates.通过脱氧核苷H-膦酸酯中间体合成DNA。
Nucleic Acids Res. 1986 Jul 11;14(13):5399-407. doi: 10.1093/nar/14.13.5399.
6
Solid phase synthesis of oligoribonucleotides using the o-nitrobenzyl group for 2'-hydroxyl protection and H-phosphonate chemistry.使用邻硝基苄基进行2'-羟基保护和H-膦酸酯化学法固相合成寡核糖核苷酸。
Nucleic Acids Res. 1987 Sep 25;15(18):7235-48. doi: 10.1093/nar/15.18.7235.