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1
Solid support synthesis of oligothymidylates using phosphorochloridates and 1-alkylimidazoles.使用氯代磷酸酯和1-烷基咪唑进行寡聚胸苷酸的固相合成。
Nucleic Acids Res. 1975 Jun;2(6):773-86. doi: 10.1093/nar/2.6.773.
2
Synthesis of oligothymidylates and nucleoside cyclic phosphates by oxidation-reduction condensation.通过氧化还原缩合合成寡聚胸苷酸和核苷环磷酸酯。
J Am Chem Soc. 1972 Nov 29;94(24):8528-32. doi: 10.1021/ja00779a039.
3
[Nucleosides and nucleotides. Solid-phase synthesis of oligonucleotides on an insoluble, macroporous carrier].[核苷与核苷酸。在不溶性大孔载体上进行寡核苷酸的固相合成]
Helv Chim Acta. 1973 Mar 14;56(2):654-70. doi: 10.1002/hlca.19730560212.
4
[Synthesis of ologonucleotides on a popcorn-polystyrene polymeric carrier].[在爆米花-聚苯乙烯聚合物载体上合成寡核苷酸]
Justus Liebigs Ann Chem. 1972 Dec;766:6-15. doi: 10.1002/jlac.19727660103.
5
Synthesis of thymidine oligonucleotides by phosphite triester intermediates.通过亚磷酸三酯中间体合成胸苷寡核苷酸。
J Am Chem Soc. 1976 Jun 9;98(12):3655-61. doi: 10.1021/ja00428a045.
6
Solid phase synthesis of polynucleotides. VI. Further studies on polystyrene copolymers for the solid support.多核苷酸的固相合成。VI. 关于用于固相载体的聚苯乙烯共聚物的进一步研究。
Nucleic Acids Res. 1982 Mar 11;10(5):1755-69. doi: 10.1093/nar/10.5.1755.
7
Oligothymidylates: formation by thermal condensation of O 2 ,5'-cyclothymidine 3'-phosphate.寡聚胸苷酸：由2,5'-环胸苷3'-磷酸的热缩合形成。
Science. 1972 Jul 21;177(4045):272-4. doi: 10.1126/science.177.4045.272.
8
The prebiotic synthesis of deoxthymidine oligonucleotides. II. Comparison of condensing agents.脱氧胸苷寡核苷酸的益生元合成。II. 缩合剂的比较。
J Mol Evol. 1975 Nov 4;6(3):199-207. doi: 10.1007/BF01732356.
9
Formation of internucleotide 3'-5' phosphoramidate links by direct coupling of phosphoryl and amino groups.通过磷酰基和氨基的直接偶联形成核苷酸间3'-5'磷酰胺键。
Nucleic Acids Res. 1975 Jul;2(7):1123-7. doi: 10.1093/nar/2.7.1123.
10
Synthesis of ppTppp via phosphotriester intermediates.通过磷酸三酯中间体合成ppTppp。
Nucleic Acids Res. 1983 Nov 11;11(21):7545-54. doi: 10.1093/nar/11.21.7545.

引用本文的文献

1
Solid-phase synthesis of polynucleotides. II. Synthesis of polythymidylic acids by the block coupling phosphotriester method.多核苷酸的固相合成。II. 用片段偶联磷酸三酯法合成聚胸腺嘧啶核苷酸
Nucleic Acids Res. 1980 Nov 25;8(22):5473-89. doi: 10.1093/nar/8.22.5473.
2
Rapid synthesis of oligodeoxyribonucleotides. IV. Improved solid phase synthesis of oligodeoxyribonucleotides through phosphotriester intermediates.寡脱氧核糖核苷酸的快速合成。IV. 通过磷酸三酯中间体改进寡脱氧核糖核苷酸的固相合成
Nucleic Acids Res. 1980 Mar 11;8(5):1081-96. doi: 10.1093/nar/8.5.1081.
3
Synthesis of oligonucleotides on cellulose by a phosphotriester method.通过磷酸三酯法在纤维素上合成寡核苷酸。
Nucleic Acids Res. 1980 May 24;8(10):2331-48. doi: 10.1093/nar/8.10.2331.
4
Syringe method for stepwise chemical synthesis of oligonucleotides.用于寡核苷酸逐步化学合成的注射器法
Nucleic Acids Res. 1982 May 25;10(10):3249-60. doi: 10.1093/nar/10.10.3249.
5
Rapid synthesis of oligodeoxyribonucleotides: a new solid-phase method.寡脱氧核糖核苷酸的快速合成：一种新的固相方法。
Nucleic Acids Res. 1977 Apr;4(4):1135-58. doi: 10.1093/nar/4.4.1135.

本文引用的文献

1
Synthetic studies of nucleic acids on polymer supports. I. Oligodeoxyribonucleotide synthesis on an insoluble polymer support.聚合物载体上核酸的合成研究。I. 不溶性聚合物载体上的寡脱氧核糖核苷酸合成。
J Chem Soc Perkin 1. 1967;22:2438-42. doi: 10.1039/j39670002438.
2
Oligonucleotide syntheses utilizing beta-benzoylpropionyl, a blocking group with a trigger for selective cleavage.利用β-苯甲酰丙酰基进行的寡核苷酸合成，β-苯甲酰丙酰基是一种带有选择性切割触发基团的保护基团。
J Am Chem Soc. 1967 Dec 20;89(26):7146-7. doi: 10.1021/ja01002a074.
3
Reactions of nucleosides on polymer supports. Synthesis of thymidylylthymidylylthymidine.聚合物载体上核苷的反应。胸苷酰胸苷酰胸苷的合成。
Biochemistry. 1967 May;6(5):1379-88. doi: 10.1021/bi00857a021.
4
Stepwise synthesis of oligodeoxyribonucleotides on an insoluble polymer support.在不溶性聚合物载体上逐步合成寡脱氧核糖核苷酸。
J Am Chem Soc. 1966 Nov 20;88(22):5319-24. doi: 10.1021/ja00974a053.
5
Synthesis of deoxyguanylyldeoxyguanosine on an insoluble polymer support.脱氧鸟苷酰脱氧鸟苷在不溶性聚合物载体上的合成。
J Org Chem. 1968 Feb;33(2):708-11. doi: 10.1021/jo01266a048.
6
A new polymer-support method for the synthesis of ribooligonucleotide.一种用于合成核糖寡核苷酸的新型聚合物支持方法。
J Am Chem Soc. 1971 Jun 30;93(13):3272-6. doi: 10.1021/ja00742a029.
7
[Synthesis of oligonucleotides on polymer carriers. Synthesis of oligodeoxynucleotides containing deoxyguanylic acid].[聚合物载体上寡核苷酸的合成。含脱氧鸟苷酸的寡脱氧核苷酸的合成]
Dokl Akad Nauk SSSR. 1971 Aug 11;199(5):1072-4.
8
Studies on transfer ribonucleic acids and related compounds. V. Synthesis of ribonucleotides with phosphomonoester end groups on a polymer support.转移核糖核酸及相关化合物的研究。V. 聚合物载体上具有磷酸单酯端基的核糖核苷酸的合成。
J Am Chem Soc. 1972 May 3;94(9):3229-33. doi: 10.1021/ja00764a055.
9
The synthesis of oligoribonucleotides. X. Preparation of 2',3'-cyclic phosphates of ribonucleosides and diribonucleoside phosphates via phosphotriester intermediates.寡核糖核苷酸的合成。X. 通过磷酸三酯中间体制备核糖核苷2',3'-环磷酸酯和二核糖核苷磷酸酯。
J Chem Soc Perkin 1. 1973;21:2513-7. doi: 10.1039/p19730002513.
10
[Nucleosides and nucleotides. Solid-phase synthesis of oligonucleotides on an insoluble, macroporous carrier].[核苷与核苷酸。在不溶性大孔载体上进行寡核苷酸的固相合成]
Helv Chim Acta. 1973 Mar 14;56(2):654-70. doi: 10.1002/hlca.19730560212.

使用氯代磷酸酯和1-烷基咪唑进行寡聚胸苷酸的固相合成。

Solid support synthesis of oligothymidylates using phosphorochloridates and 1-alkylimidazoles.

作者信息

Pless R C, Letsinger R L

出版信息

Nucleic Acids Res. 1975 Jun;2(6):773-86. doi: 10.1093/nar/2.6.773.

DOI:10.1093/nar/2.6.773
PMID:167350
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC343465/
Abstract

A study of the synthesis of oligothymidylates via phosphotriester intermediates on a polystyrene support is described. The sequence involves condensation of a phenyl nucleoside-3' -phosphorochloridate with the 5'-hydroxyl group of the carrier bound oligonucleotide derivative in the presence of 1-methylimidazole. Conditions for preparation of the phenyl nucleo-side phosphorochloridate as well as for the condensation on the support are discussed. d-TpTpTpT was obtained in 31% overall yield from carrier bound thymidine in one series of experiments, and d-TpTpTpTpT was obtained in 9% yield in another. The cycle for addition of one nucleotide unit can be completed in about six hours.

摘要

本文描述了一项在聚苯乙烯载体上通过磷酸三酯中间体合成寡聚胸苷酸的研究。该序列包括在1-甲基咪唑存在下，苯基核苷-3'-磷酰氯与载体结合的寡核苷酸衍生物的5'-羟基缩合。讨论了制备苯基核苷磷酰氯以及在载体上进行缩合的条件。在一系列实验中，从载体结合的胸苷中以31%的总收率获得了d-TpTpTpT，在另一实验中，以9%的收率获得了d-TpTpTpTpT。添加一个核苷酸单元的循环大约可在6小时内完成。