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1
The isopropoxyacetic group for convenient base protection during solid-support synthesis of oligodeoxyribonucleotides and their triester analogs.异丙氧基乙酰基用于在寡脱氧核糖核苷酸及其三酯类似物的固相合成过程中方便地进行碱基保护。
Nucleic Acids Res. 1989 Jun 26;17(12):4863-71. doi: 10.1093/nar/17.12.4863.
2
Improved synthesis of oligodeoxyribonucleotide using 3-methoxy-4-phenoxybenzoyl group for amino protection.使用3-甲氧基-4-苯氧基苯甲酰基进行氨基保护改进寡脱氧核糖核苷酸的合成。
Nucleic Acids Res. 1986 Aug 11;14(15):6197-213. doi: 10.1093/nar/14.15.6197.
3
A rapid deprotection procedure for phosphotriester DNA synthesis.一种用于磷酸三酯DNA合成的快速脱保护程序。
Nucleic Acids Res. 1984 Sep 11;12(17):6853-9. doi: 10.1093/nar/12.17.6853.
4
Mass spectrometric monitoring of solid phase phosphate triester synthesis of DNA fragments.DNA片段固相磷酸三酯合成的质谱监测
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Chemical stability of 2'-deoxy-5-methylisocytidine during oligodeoxynucleotide synthesis and deprotection.
Nucleosides Nucleotides Nucleic Acids. 2002 Jun-Jul;21(6-7):417-26. doi: 10.1081/NCN-120014814.
6
Polymer support synthesis of oligodeoxyribonucleotide with an aminoethyl or aminohexyl group at the 5' end by the phosphite-triester approach.通过亚磷酸三酯法在聚合物载体上合成5'端带有氨乙基或氨己基的寡脱氧核糖核苷酸。
Chem Pharm Bull (Tokyo). 1988 Apr;36(4):1386-92. doi: 10.1248/cpb.36.1386.
7
Multiple oligodeoxyribonucleotide syntheseson a reusable solid-phase CPG support via the hydroquinone-O,O'-diacetic acid (Q-Linker) linker arm.通过对苯二酚 - O,O'-二乙酸（Q - 连接体）连接臂在可重复使用的固相CPG载体上进行多个寡脱氧核糖核苷酸的合成。
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Unexpected chain-terminating side reaction caused by histidine and acetic anhydride in solid-phase peptide synthesis.固相肽合成中由组氨酸和乙酸酐引起的意外链终止副反应。
Chem Pharm Bull (Tokyo). 1989 Feb;37(2):506-8. doi: 10.1248/cpb.37.506.
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Synthesis of well-defined phosphate-methylated DNA fragments: the application of potassium carbonate in methanol as deprotecting reagent.合成明确的磷酸甲基化DNA片段：碳酸钾在甲醇中作为去保护试剂的应用。
Nucleic Acids Res. 1990 Sep 11;18(17):5197-205. doi: 10.1093/nar/18.17.5197.
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The final deprotection step in oligonucleotide synthesis is reduced to a mild and rapid ammonia treatment by using labile base-protecting groups.通过使用不稳定的碱基保护基团，寡核苷酸合成中的最终脱保护步骤简化为温和且快速的氨处理。
Nucleic Acids Res. 1987 Jan 26;15(2):397-416. doi: 10.1093/nar/15.2.397.

引用本文的文献

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Modified internucleoside linkages for nuclease-resistant oligonucleotides.用于抗核酸酶寡核苷酸的修饰核苷间连接。
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Application of activated nucleoside analogs for the treatment of drug-resistant tumors by oral delivery of nanogel-drug conjugates.通过口服纳米凝胶药物偶联物应用激活的核苷类似物治疗耐药性肿瘤。
J Control Release. 2013 Apr 28;167(2):200-9. doi: 10.1016/j.jconrel.2013.01.020. Epub 2013 Feb 4.
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Significance of stereochemistry of 3'-terminal phosphorothioate-modified primer in DNA polymerase-mediated chain extension.3'-末端硫代磷酸酯修饰引物的立体化学在DNA聚合酶介导的链延伸中的意义
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4
Advanced method for oligonucleotide deprotection.寡核苷酸脱保护的先进方法。
Nucleic Acids Res. 2000 Apr 15;28(8):E29. doi: 10.1093/nar/28.8.e29.
5
Cleavage of oligodeoxyribonucleotides from controlled-pore glass supports and their rapid deprotection by gaseous amines.从可控孔径玻璃载体上切割寡脱氧核糖核苷酸及其通过气态胺进行的快速脱保护。
Nucleic Acids Res. 1996 Aug 1;24(15):3115-7. doi: 10.1093/nar/24.15.3115.
6
On the rapid deprotection of synthetic oligonucleotides and analogs.关于合成寡核苷酸及其类似物的快速脱保护
Nucleic Acids Res. 1994 Feb 25;22(4):639-45. doi: 10.1093/nar/22.4.639.
7
Antisense pro-drugs: 5'-ester oligodeoxynucleotides.反义前药：5'-酯寡脱氧核苷酸。
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8
Expression and characterization of the multiplied, recombinant preS1 antigen of hepatitis B virus.乙型肝炎病毒增殖重组前S1抗原的表达与鉴定
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本文引用的文献

1
The final deprotection step in oligonucleotide synthesis is reduced to a mild and rapid ammonia treatment by using labile base-protecting groups.通过使用不稳定的碱基保护基团，寡核苷酸合成中的最终脱保护步骤简化为温和且快速的氨处理。
Nucleic Acids Res. 1987 Jan 26;15(2):397-416. doi: 10.1093/nar/15.2.397.
2
Alkyl phosphotriester modified oligodeoxyribonucleotides. V. Synthesis and absolute configuration of Rp and Sp diastereomers of an ethyl phosphotriester (Et) modified EcoRI recognition sequence, d[GGAA(Et)TTCC]. A synthetic approach to regio- and stereospecific ethylation-interference studies.烷基磷酸三酯修饰的寡脱氧核糖核苷酸。V. 磷酸三乙酯（Et）修饰的EcoRI识别序列d[GGAA(Et)TTCC]的Rp和Sp非对映异构体的合成及绝对构型。区域和立体特异性乙基干扰研究的合成方法。
Nucleic Acids Res. 1986 Sep 25;14(18):7405-20. doi: 10.1093/nar/14.18.7405.
3
Letter: Phosphite coupling procedure for generating internucleotide links.信函：用于生成核苷酸间连接的亚磷酸酯偶联方法。
J Am Chem Soc. 1975 May 28;97(11):3278-9. doi: 10.1021/ja00844a090.

异丙氧基乙酰基用于在寡脱氧核糖核苷酸及其三酯类似物的固相合成过程中方便地进行碱基保护。

The isopropoxyacetic group for convenient base protection during solid-support synthesis of oligodeoxyribonucleotides and their triester analogs.

作者信息

Uznanski B, Grajkowski A, Wilk A

机构信息

Polish Academy of Sciences, Department of Bioorganic Chemistry, Lodz.

出版信息

Nucleic Acids Res. 1989 Jun 26;17(12):4863-71. doi: 10.1093/nar/17.12.4863.

DOI:10.1093/nar/17.12.4863
PMID:2748339
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC318037/
Abstract

Isopropoxyacetic anhydride was successfully used for protection of exoaminofunctions of 2'-deoxyadenosine, -guanosine and -cytidine. N-isopropoxyacetylated nucleosides are stable under the conditions of the synthesis of oligodeoxyribonucleotides on the solid support. Removal of N-isopropoxyacetyl is much faster than that of commonly used benzoyl or isobutyryl groups viz. it is completed within the operation of cleavage of the oligodeoxyribonucleotide from the solid support. This observation enabled synthesis of -OCH2CH3 and -OCH2CF3 triesters, which hydrolyse partially or completely when standard deprotection conditions are applied.

摘要

异丙氧基乙酸酐已成功用于保护2'-脱氧腺苷、-鸟苷和-胞苷的氨基外官能团。N-异丙氧基乙酰化核苷在固体支持物上合成寡脱氧核糖核苷酸的条件下是稳定的。N-异丙氧基乙酰基的去除比常用的苯甲酰基或异丁酰基快得多，即在从固体支持物上切割寡脱氧核糖核苷酸的操作过程中即可完成。这一发现使得-OCH2CH3和-OCH2CF3三酯得以合成，当应用标准脱保护条件时，它们会部分或完全水解。