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1
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.
2
Highly efficient synthesis of oligodeoxyribonucleotides using alpha-phenyl cinnamoyl group for selective amino protection.使用α-苯基肉桂酰基进行选择性氨基保护高效合成寡脱氧核糖核苷酸。
Nucleic Acids Res. 1989 Jul 11;17(13):5125-34. doi: 10.1093/nar/17.13.5125.
3
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.
4
Rapid synthesis of oligodeoxyribonucleotides. V. Further studies in solid phase synthesis of oligodeoxyribonucleotides through phosphotriester intermediates.寡聚脱氧核糖核苷酸的快速合成。V. 通过磷酸三酯中间体进行寡聚脱氧核糖核苷酸固相合成的进一步研究。
Nucleic Acids Symp Ser. 1980(7):243-57.
5
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.
6
Cyclic diacyl groups for protection of the N6-amino group of deoxyadenosine in oligodeoxynucleotide synthesis.用于在寡脱氧核苷酸合成中保护脱氧腺苷N6-氨基的环状二酰基基团。
Nucleic Acids Res. 1984 Nov 26;12(22):8525-38. doi: 10.1093/nar/12.22.8525.
7
Synthesis of oligodeoxyribonucleotide with aliphatic amino or phosphate group at the 5' end by the phosphotriester method on a polystyrene support.在聚苯乙烯载体上通过磷酸三酯法合成5'端带有脂肪族氨基或磷酸基团的寡脱氧核糖核苷酸。
Nucleic Acids Res. 1987 Aug 11;15(15):6209-24. doi: 10.1093/nar/15.15.6209.
8
Synthesis of high quality phosphorothioate oligonucleotides as antisense drugs. Use of I-linker in the elimination of 3'-terminal phosphorothioate monoesters.高质量硫代磷酸酯寡核苷酸作为反义药物的合成。I-连接体在消除3'-末端硫代磷酸单酯中的应用。
Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):1421-5. doi: 10.1081/NCN-120023000.
9
Synthesis of oligodeoxyribonucleotides by solid phase phosphotriester method on a reduced scale; preparation of oligonucleotides for improved promoter sequence.在小规模下通过固相磷三酯法合成寡脱氧核糖核苷酸；制备用于改进启动子序列的寡核苷酸。
Nucleic Acids Symp Ser. 1982(11):77-80.
10
Chemical synthesis and properties of an oligodeoxyribonucleotide containing a 2-deoxyribosylformamide residue.含有2-脱氧核糖基甲酰胺残基的寡脱氧核糖核苷酸的化学合成与性质
Chem Pharm Bull (Tokyo). 1993 May;41(5):961-4. doi: 10.1248/cpb.41.961.

引用本文的文献

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
Highly efficient synthesis of oligodeoxyribonucleotides using alpha-phenyl cinnamoyl group for selective amino protection.使用α-苯基肉桂酰基进行选择性氨基保护高效合成寡脱氧核糖核苷酸。
Nucleic Acids Res. 1989 Jul 11;17(13):5125-34. doi: 10.1093/nar/17.13.5125.

本文引用的文献

1
Synthesis of 1-N-oxides of deoxyadenosine and deoxyadenosine monophosphate.脱氧腺苷和脱氧腺苷一磷酸1-N-氧化物的合成。
Biochim Biophys Acta. 1961 Sep 16;52:384-6. doi: 10.1016/0006-3002(61)90691-6.
2
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。
Nucleic Acids Res. 1982 Oct 25;10(20):6243-54. doi: 10.1093/nar/10.20.6243.
3
Dialkylformamidines: depurination resistant N6-protecting group for deoxyadenosine.二烷基甲脒：用于脱氧腺苷的抗脱嘌呤N6保护基团。
Nucleic Acids Res. 1983 Nov 25;11(22):8031-6. doi: 10.1093/nar/11.22.8031.
4
Solvolysis of adenine nucleosides. I. Effects of sugars and adenine substituents on acid solvolyses.腺嘌呤核苷的溶剂解。I. 糖类和腺嘌呤取代基对酸溶剂解的影响。
J Am Chem Soc. 1972 Nov 29;94(24):8532-41. doi: 10.1021/ja00779a040.
5
CV. Total synthesis of the structural gene for an alanine transfer ribonucleic acid from yeast. Chemical synthesis of an icosadeoxyribonucleotide corresponding to the nucleotide sequence 31 to 50.简历。酵母丙氨酸转移核糖核酸结构基因的全合成。对应于核苷酸序列31至50的二十碳脱氧核糖核苷酸的化学合成。
J Mol Biol. 1972 Dec 28;72(2):251-88. doi: 10.1016/0022-2836(72)90148-9.
6
Platelet aggregation inhibitors. IX. Chemical transformation of adenosine into 2-thioadenosine derivatives.血小板聚集抑制剂。IX。腺苷向2-硫代腺苷衍生物的化学转化。
Chem Pharm Bull (Tokyo). 1977 Aug;25(8):1959-69. doi: 10.1248/cpb.25.1959.
7
Use of the lipophilic tert-butyldiphenylsilyl protecting group in synthesis and rapid separation of polynucleotides.亲脂性叔丁基二苯基硅烷基保护基团在多核苷酸合成及快速分离中的应用。
Biochemistry. 1978 Apr 4;17(7):1268-78. doi: 10.1021/bi00600a021.
8
Arylsulfonyltetrazoles, new coupling reagents and further improvements in the triester method for the synthesis of deoxyribooligonucleotides.芳基磺酰四唑，新型偶联试剂以及脱氧核糖寡核苷酸合成三酯法的进一步改进。
Nucleic Acids Res. 1977 Feb;4(2):353-71. doi: 10.1093/nar/4.2.353.

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。

Improved synthesis of oligodeoxyribonucleotide using 3-methoxy-4-phenoxybenzoyl group for amino protection.

作者信息

Mishra R K, Misra K

出版信息

Nucleic Acids Res. 1986 Aug 11;14(15):6197-213. doi: 10.1093/nar/14.15.6197.

DOI:10.1093/nar/14.15.6197
PMID:3748807
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC311631/
Abstract

3-Methoxy-4-phenoxybenzoyl group has been used for the protection of exocyclic amino group of nucleosides. In case of 2'-deoxycytidine it has been found to be highly selective under controlled conditions. The N-protected derivatives of 2'-deoxyadenosine and 2'-deoxyguanosine have been found to be sufficiently stable towards acids minimising depurination under conditions of synthesis of oligodeoxyribonucleotide on solid support via phosphotriester approach. The high lipophilicity of the group and milder deprotection conditions are additional advantages.

摘要

3-甲氧基-4-苯氧基苯甲酰基已用于核苷外环氨基的保护。在2'-脱氧胞苷的情况下，已发现在可控条件下它具有高度选择性。2'-脱氧腺苷和2'-脱氧鸟苷的N-保护衍生物已被发现对酸具有足够的稳定性，在通过磷酸三酯法在固体支持物上合成寡脱氧核糖核苷酸的条件下，可将脱嘌呤作用降至最低。该基团的高亲脂性和较温和的脱保护条件是额外的优点。