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硫代磷酸酯修饰的寡脱氧核糖核苷酸。III. 源自非对映体O-乙基硫代磷酸酯的Rp-Rp、Sp-Sp和Rp-Sp双链体[d(GGSAATTCC)]2的核磁共振和紫外光谱研究。

Phosphorothioate-modified oligodeoxyribonucleotides. III. NMR and UV spectroscopic studies of the Rp-Rp, Sp-Sp, and Rp-Sp duplexes, [d(GGSAATTCC)]2, derived from diastereomeric O-ethyl phosphorothioates.

作者信息

LaPlanche L A, James T L, Powell C, Wilson W D, Uznanski B, Stec W J, Summers M F, Zon G

出版信息

Nucleic Acids Res. 1986 Nov 25;14(22):9081-93. doi: 10.1093/nar/14.22.9081.

DOI:10.1093/nar/14.22.9081
PMID:3786144
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC311930/
Abstract

2D-NOE and 1H NMR chemical shift data obtained for the title oligonucleotides were compared with similar data previously reported [Broido et al. (1985) Eur. J. Biochem. 150, 117-128] for the unmodified "parent" structure, [d(GGAATTCC)]2. The spectroscopically detectable structural perturbations caused by replacement of phosphate oxygen with sulfur were mostly localized within the GsA moiety, and were greater for the Rp configuration wherein sulfur is oriented into the major groove of the B-helix. UV-derived Tm measurements gave the following order of stability for the duplexes in 0.4 M NaCl: unmodified (33.9 +/- 0.1 degrees C) approximately Sp-Sp (34.1 degrees C) greater than Rp-Rp (31.7 degrees C). The title compounds were prepared by a new and convenient synthetic route which utilized HPLC to separate the diastereomeric O-ethyl phosphorothioate precursors, (Rp)- and (Sp)-d[GG(S,Et)AATTCC], for subsequent de-ethylation by ammonia in water.

摘要

将所获得的标题寡核苷酸的二维核Overhauser效应（2D-NOE）和氢核磁共振（1H NMR）化学位移数据，与先前报道的[布罗伊多等人（1985年）《欧洲生物化学杂志》150卷，第117 - 128页]未修饰的“亲本”结构[d（GGAATTCC）]2的类似数据进行了比较。由硫取代磷酸氧所引起的可通过光谱检测到的结构扰动，大多局限于鸟嘌呤-腺嘌呤（GsA）部分，并且对于硫朝向B型螺旋大沟的Rp构型而言扰动更大。紫外衍生的熔解温度（Tm）测量给出了在0.4M氯化钠中双链体稳定性的以下顺序：未修饰的（33.9±0.1℃）≈Sp-Sp（34.1℃）＞Rp-Rp（31.7℃）。标题化合物是通过一种新的便捷合成路线制备的，该路线利用高效液相色谱（HPLC）分离非对映体的O-乙基硫代磷酸酯前体，即（Rp）-和（Sp）-d[GG（S，Et）AATTCC]，随后在水中用氨进行脱乙基反应。

相似文献

1
Phosphorothioate-modified oligodeoxyribonucleotides. III. NMR and UV spectroscopic studies of the Rp-Rp, Sp-Sp, and Rp-Sp duplexes, [d(GGSAATTCC)]2, derived from diastereomeric O-ethyl phosphorothioates.硫代磷酸酯修饰的寡脱氧核糖核苷酸。III. 源自非对映体O-乙基硫代磷酸酯的Rp-Rp、Sp-Sp和Rp-Sp双链体[d(GGSAATTCC)]2的核磁共振和紫外光谱研究。
Nucleic Acids Res. 1986 Nov 25;14(22):9081-93. doi: 10.1093/nar/14.22.9081.
2
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Synthesis and characterization of an octanucleotide containing the EcoRI recognition sequence with a phosphorothioate group at the cleavage site.一种在切割位点含有硫代磷酸酯基团的含EcoRI识别序列的八核苷酸的合成与表征。
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Proton nuclear magnetic resonance investigation of the conformation and dynamics in the synthetic deoxyribonucleic acid decamers d(ATATCGATAT) and d(ATATGCATAT).合成脱氧核糖核酸十聚体d(ATATCGATAT)和d(ATATGCATAT)的构象与动力学的质子核磁共振研究
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Synthesis of phosphorothioate-containing DNA fragments by a modified hydroxybenzotriazole phosphotriester approach.通过改良的羟基苯并三唑磷酸三酯方法合成含硫代磷酸酯的DNA片段。
Nucleic Acids Res. 1984 Dec 11;12(23):9095-110. doi: 10.1093/nar/12.23.9095.
7
Left-handed DNA: from synthetic polymers to chromosomes.左手螺旋DNA：从合成聚合物到染色体
J Biomol Struct Dyn. 1983 Oct;1(1):21-57. doi: 10.1080/07391102.1983.10507425.
8
Assignment of resonances in the phosphorus-31 nuclear magnetic resonance spectrum of poly[d(A-T)] from phosphorothioate substitution.通过硫代磷酸酯取代对聚[d(A-T)]的磷-31核磁共振谱中的共振进行归属。
Biochemistry. 1983 Sep 13;22(19):4546-50. doi: 10.1021/bi00288a030.
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Sequence-specific recognition of DNA: assignment of nonexchangeable proton resonances in the consensus Pribnow promoter DNA sequence by two-dimensional NMR.DNA的序列特异性识别：通过二维核磁共振确定共有普里布诺启动子DNA序列中不可交换质子的共振归属
Biochemistry. 1984 May 8;23(10):2262-8. doi: 10.1021/bi00305a027.
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Recognition by restriction endonuclease EcoRI of deoxyoctanucleotides containing modified sugar moieties.限制性内切酶EcoRI对含有修饰糖基部分的脱氧八聚核苷酸的识别。
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