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。
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.
作者信息
Nielsen J, Taagaard M, Marugg J E, van Boom J H, Dahl O
出版信息
Nucleic Acids Res. 1986 Sep 25;14(18):7391-403. doi: 10.1093/nar/14.18.7391.
Abstract
Deoxyribonucleoside phosphoramidites are prepared in situ from 5'-O,N-protected deoxyribonucleosides and 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite with tetrazole as catalyst, and the solutions applied directly on an automatic solid-phase DNA synthesizer. Using LCAA-CPG support and a cycle time of 12.5 min, oligonucleotides of 16-25 bases are obtained with a DMT-efficiency per cycle of 98.0-99.3%. The crude and fully deblocked products are of a purity comparable to that obtained using purified phosphoramidites. In case of d(G)16 the product was difficult to analyse and a better product was not obtained using doubly protected (O-6 diphenylcarbamoyl) guanine.
摘要
脱氧核苷亚磷酰胺是由5'-O,N-保护的脱氧核苷和2-氰基乙基N,N,N',N'-四异丙基亚磷二酰胺在四唑作为催化剂的条件下原位制备的，所得溶液直接应用于自动固相DNA合成仪。使用LCAA-CPG载体和12.5分钟的循环时间，可获得16 - 25个碱基的寡核苷酸，每个循环的DMT效率为98.0 - 99.3%。粗产物和完全脱保护的产物的纯度与使用纯化的亚磷酰胺所获得的纯度相当。对于d(G)16，产物难以分析，并且使用双保护（O-6二苯基甲酰基）鸟嘌呤也未获得更好的产物。
相似文献
1
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.
2
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.
3
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.
4
Modification of guanine bases by nucleoside phosphoramidite reagents during the solid phase synthesis of oligonucleotides.在寡核苷酸固相合成过程中，鸟嘌呤碱基被核苷亚磷酰胺试剂修饰。
Nucleic Acids Res. 1985 Sep 25;13(18):6447-65. doi: 10.1093/nar/13.18.6447.
5
The synthesis of protected 5'-mercapto-2',5'-dideoxyribonucleoside-3'-O-phosphoramidites; uses of 5'-mercapto-oligodeoxyribonucleotides.受保护的5'-巯基-2',5'-二脱氧核糖核苷-3'-O-亚磷酰胺的合成；5'-巯基寡脱氧核糖核苷酸的用途。
Nucleic Acids Res. 1987 Jun 25;15(12):4837-48. doi: 10.1093/nar/15.12.4837.
6
Solid-phase syntheses of oligodeoxyribonucleoside methylphosphonates.寡脱氧核糖核苷甲基膦酸酯的固相合成
Biochemistry. 1986 Sep 9;25(18):5092-7. doi: 10.1021/bi00366a017.
7
The 3-(N-tert-butylcarboxamido)-1-propyl group as an attractive phosphate/thiophosphate protecting group for solid-phase oligodeoxyribonucleotide synthesis.3-(N-叔丁基甲酰胺基)-1-丙基作为用于固相寡脱氧核糖核苷酸合成的一种有吸引力的磷酸酯/硫代磷酸酯保护基团。
J Org Chem. 2002 Sep 6;67(18):6430-8. doi: 10.1021/jo0258608.
8
Selective O-phosphitilation with nucleoside phosphoramidite reagents.使用核苷亚磷酰胺试剂进行选择性O-磷酰化反应。
Nucleic Acids Res. 1992 Apr 25;20(8):1879-82. doi: 10.1093/nar/20.8.1879.
9
Analytical studies of 'mixed sequence' oligodeoxyribonucleotides synthesized by competitive coupling of either methyl- or beta-cyanoethyl-N,N-diisopropylamino phosphoramidite reagents, including 2'-deoxyinosine.对通过甲基或β-氰基乙基-N,N-二异丙基氨基亚磷酰胺试剂（包括2'-脱氧次黄苷）的竞争性偶联合成的“混合序列”寡脱氧核糖核苷酸的分析研究。
Nucleic Acids Res. 1985 Nov 25;13(22):8181-96. doi: 10.1093/nar/13.22.8181.
10
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.
引用本文的文献
1
Click Chemistry Methodology: The Novel Paintbrush of Drug Design.点击化学方法：药物设计的新型画笔。
ACS Chem Biol. 2025 Jan 17;20(1):19-32. doi: 10.1021/acschembio.4c00608. Epub 2024 Dec 27.
2
Synthesis of Substituted Cy5 Phosphoramidite Derivatives and Their Incorporation into Oligonucleotides Using Automated DNA Synthesis.取代的Cy5亚磷酰胺衍生物的合成及其通过自动DNA合成掺入寡核苷酸。
ACS Omega. 2022 Mar 22;7(13):11002-11016. doi: 10.1021/acsomega.1c06921. eCollection 2022 Apr 5.
3
Retracted Article: Divergent synthesis of 5-substituted pyrimidine 2'-deoxynucleosides and their incorporation into oligodeoxynucleotides for the survey of uracil DNA glycosylases.撤回文章：5-取代嘧啶2'-脱氧核苷的发散合成及其掺入寡脱氧核苷酸以用于尿嘧啶DNA糖基化酶的研究
Chem Sci. 2020 Oct 7;11(43):11818-11826. doi: 10.1039/d0sc04161k.
4
On-demand synthesis of phosphoramidites.按需合成膦酰胺。
Nat Commun. 2021 May 12;12(1):2760. doi: 10.1038/s41467-021-22945-z.
5
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.
6
Metal-bipyridine complexes in DNA backbones and effects on thermal stability.金属联吡啶配合物在 DNA 骨架中的作用及其对热稳定性的影响。
J Biol Inorg Chem. 2010 Jun;15(5):629-39. doi: 10.1007/s00775-010-0630-5. Epub 2010 Feb 26.
7
Polymerase incorporation and miscoding properties of 5-chlorouracil.5-氯尿嘧啶的聚合酶掺入和错配性质。
Chem Res Toxicol. 2010 Apr 19;23(4):740-8. doi: 10.1021/tx900302j.
8
5-halogenated pyrimidine lesions within a CpG sequence context mimic 5-methylcytosine by enhancing the binding of the methyl-CpG-binding domain of methyl-CpG-binding protein 2 (MeCP2).在CpG序列环境中的5-卤代嘧啶损伤通过增强甲基-CpG结合蛋白2（MeCP2）的甲基-CpG结合结构域的结合来模拟5-甲基胞嘧啶。
Nucleic Acids Res. 2005 May 25;33(9):3057-64. doi: 10.1093/nar/gki612. Print 2005.
9
Oxidative damage to methyl-CpG sequences inhibits the binding of the methyl-CpG binding domain (MBD) of methyl-CpG binding protein 2 (MeCP2).甲基-CpG序列的氧化损伤会抑制甲基-CpG结合蛋白2（MeCP2）的甲基-CpG结合结构域（MBD）的结合。
Nucleic Acids Res. 2004 Aug 9;32(14):4100-8. doi: 10.1093/nar/gkh739. Print 2004.
10
Synthesis of stable-isotope enriched 5-methylpyrimidines and their use as probes of base reactivity in DNA.稳定同位素富集的5-甲基嘧啶的合成及其作为DNA中碱基反应性探针的应用。
Nucleic Acids Res. 2002 Sep 15;30(18):4068-74. doi: 10.1093/nar/gkf520.
本文引用的文献
1
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。
Nucleic Acids Res. 1983 May 11;11(9):2575-84. doi: 10.1093/nar/11.9.2575.
2
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.
3
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.
4
Synthesis and use of synthetic oligonucleotides.合成寡核苷酸的合成与应用。
Annu Rev Biochem. 1984;53:323-56. doi: 10.1146/annurev.bi.53.070184.001543.
5
6
Analytical studies of 'mixed sequence' oligodeoxyribonucleotides synthesized by competitive coupling of either methyl- or beta-cyanoethyl-N,N-diisopropylamino phosphoramidite reagents, including 2'-deoxyinosine.对通过甲基或β-氰基乙基-N,N-二异丙基氨基亚磷酰胺试剂（包括2'-脱氧次黄苷）的竞争性偶联合成的“混合序列”寡脱氧核糖核苷酸的分析研究。
Nucleic Acids Res. 1985 Nov 25;13(22):8181-96. doi: 10.1093/nar/13.22.8181.
7
Modification of guanine bases by nucleoside phosphoramidite reagents during the solid phase synthesis of oligonucleotides.在寡核苷酸固相合成过程中，鸟嘌呤碱基被核苷亚磷酰胺试剂修饰。
Nucleic Acids Res. 1985 Sep 25;13(18):6447-65. doi: 10.1093/nar/13.18.6447.
8
Methylation of thymine residues during oligonucleotide synthesis.寡核苷酸合成过程中胸腺嘧啶残基的甲基化
Nucleic Acids Res. 1985 Jan 25;13(2):573-84. doi: 10.1093/nar/13.2.573.
9
Gene synthesis machines: DNA chemistry and its uses.基因合成机器：DNA化学及其应用
Science. 1985 Oct 18;230(4723):281-5. doi: 10.1126/science.3863253.
Zotero 插件