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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.

DOI:10.1093/nar/14.18.7391
PMID:3763407
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC311758/
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
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本文引用的文献

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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。
Nucleic Acids Res. 1983 May 11;11(9):2575-84. doi: 10.1093/nar/11.9.2575.
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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.
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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
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Base modification and cloning efficiency of oligodeoxyribonucleotides synthesized by the phosphoramidite method: methyl versus cyanoethyl phosphorus protection.亚磷酰胺法合成的寡脱氧核糖核苷酸的碱基修饰与克隆效率：甲基与氰乙基磷保护
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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.
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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.
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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.