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.
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。
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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.
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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.
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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.
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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。
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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]
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