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DNA的磷酰胺酯类似物:异源双链体的合成与热稳定性

Phosphoramidate analogues of DNA: synthesis and thermal stability of heteroduplexes.

作者信息

Froehler B, Ng P, Matteucci M

机构信息

Department of Molecular Biology, Genentech, Inc., South San Francisco, CA 94080.

出版信息

Nucleic Acids Res. 1988 Jun 10;16(11):4831-9. doi: 10.1093/nar/16.11.4831.

DOI:10.1093/nar/16.11.4831
PMID:3387210
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC336699/
Abstract

The deoxyoligonucleotide 5' AATCGGGCATGGATT (15-mer) was synthesized containing 12 phosphoramidate linkages derived from 2 primary and 2 secondary amines. The oligonucleotides were purified by reverse phase HPLC and characterized by PAGE. The thermal stability of the duplexes derived from these compounds, when hybridized to the complementary diester linked oligomer, were determined and compared to the diester and methanephosphonate oligomer. The results indicated that all analogue oligomers form less stable duplexes then the diester oligomer. A large difference was observed between primary and secondary amine derived phosphoramidates.

摘要

合成了脱氧寡核苷酸5'AATCGGGCATGGATT(15聚体),其含有12个源自2个伯胺和2个仲胺的氨基磷酸酯键。寡核苷酸通过反相高效液相色谱法纯化,并通过聚丙烯酰胺凝胶电泳进行表征。测定了这些化合物衍生的双链体与互补的二酯连接寡聚物杂交时的热稳定性,并与二酯和甲膦酸酯寡聚物进行比较。结果表明,所有类似物寡聚物形成的双链体稳定性均低于二酯寡聚物。在伯胺和仲胺衍生的氨基磷酸酯之间观察到很大差异。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e91e/336699/8b416f13c027/nar00154-0095-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e91e/336699/8b416f13c027/nar00154-0095-a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e91e/336699/8b416f13c027/nar00154-0095-a.jpg

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本文引用的文献

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Complementary oligonucleotide probe of vesicular stomatitus virus matrix protein mRNA translation.水疱性口炎病毒基质蛋白mRNA翻译的互补寡核苷酸探针。
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Oligodeoxynucleoside phosphoramidates (P-NH2): synthesis and thermal stability of duplexes with DNA and RNA targets.寡脱氧核苷亚磷酰胺酯(P-NH2):与DNA和RNA靶标的双链体的合成及热稳定性
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Solid-phase synthesis and hybridization properties of DNA containing sulfide-linked dinucleosides.含硫醚连接二核苷的DNA的固相合成及杂交性质
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Intracellular disposition and metabolism of fluorescently-labeled unmodified and modified oligonucleotides microinjected into mammalian cells.微注射到哺乳动物细胞中的荧光标记的未修饰和修饰寡核苷酸的细胞内分布与代谢
Nucleic Acids Res. 1993 Aug 11;21(16):3857-65. doi: 10.1093/nar/21.16.3857.
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Evaluation of some properties of a phosphorodithioate oligodeoxyribonucleotide for antisense application.用于反义应用的二硫代磷酸酯寡脱氧核糖核苷酸的某些性质评估。
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Oligonucleotides with novel, cationic backbone substituents: aminoethylphosphonates.具有新型阳离子主链取代基的寡核苷酸:氨乙基膦酸酯。
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用于核磁共振研究的十脱氧核糖核苷酸螺旋的制备
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