• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

双螺旋阿拉伯糖核酸（ANA 和 2'F-ANA）的溶液结构：阿拉伯糖在双链发夹互变中的作用。

The solution structure of double helical arabino nucleic acids (ANA and 2'F-ANA): effect of arabinoses in duplex-hairpin interconversion.

机构信息

Instituto de Química Física Rocasolano, CSIC, C/Serrano 119, 28006 Madrid, Spain.

出版信息

Nucleic Acids Res. 2012 Oct;40(18):9329-39. doi: 10.1093/nar/gks672. Epub 2012 Jul 14.

DOI:10.1093/nar/gks672
PMID:22798499
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3467067/
Abstract

We report here the first structure of double helical arabino nucleic acid (ANA), the C2'-stereoisomer of RNA, and the 2'-fluoro-ANA analogue (2'F-ANA). A chimeric dodecamer based on the Dickerson sequence, containing a contiguous central segment of arabino nucleotides, flanked by two 2'-deoxy-2'F-ANA wings was studied. Our data show that this chimeric oligonucleotide can adopt two different structures of comparable thermal stabilities. One structure is a monomeric hairpin in which the stem is formed by base paired 2'F-ANA nucleotides and the loop by unpaired ANA nucleotides. The second structure is a bimolecular duplex, with all the nucleotides (2'F-ANA and ANA) forming Watson-Crick base pairs. The duplex structure is canonical B-form, with all arabinoses adopting a pure C2'-endo conformation. In the ANA:ANA segment, steric interactions involving the 2'-OH substituent provoke slight changes in the glycosidic angles and, therefore, in the ANA:ANA base pair geometry. These distortions are not present in the 2'F-ANA:2'F-ANA regions of the duplex, where the -OH substituent is replaced by a smaller fluorine atom. 2'F-ANA nucleotides adopt the C2'-endo sugar pucker and fit very well into the geometry of B-form duplex, allowing for favourable 2'F···H8 interactions. This interaction shares many features of pseudo-hydrogen bonds previously observed in 2'F-ANA:RNA hybrids and in single 2'F-ANA nucleotides.

摘要

我们在此报告了双螺旋阿拉伯糖核酸（ANA）的首个结构，即 RNA 的 C2'-对映异构体，以及 2'-氟代 ANA 类似物（2'F-ANA）。研究了基于 Dickerson 序列的嵌合十二聚体，其中包含连续的阿拉伯糖核苷酸中央片段，两侧为两个 2'-脱氧-2'F-ANA 翅膀。我们的数据表明，这种嵌合寡核苷酸可以采用两种具有相当热稳定性的不同结构。一种结构是单体发夹，其中茎由碱基配对的 2'F-ANA 核苷酸形成，环由未配对的 ANA 核苷酸形成。第二种结构是双分子双链体，所有核苷酸（2'F-ANA 和 ANA）均形成 Watson-Crick 碱基对。双链体结构是典型的 B 型，所有阿拉伯糖均采用纯 C2'-内消旋构象。在 ANA:ANA 段，涉及 2'-OH 取代基的空间相互作用引起糖苷角的轻微变化，因此 ANA:ANA 碱基对几何形状发生变化。这些扭曲在双链体的 2'F-ANA:2'F-ANA 区域中不存在，其中-OH 取代基被较小的氟原子取代。2'F-ANA 核苷酸采用 C2'-内消旋糖构象，非常适合 B 型双链体的几何形状，允许有利的 2'F···H8 相互作用。这种相互作用具有以前在 2'F-ANA:RNA 杂种和单个 2'F-ANA 核苷酸中观察到的假氢键的许多特征。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/126c/3467067/a5f60ba8bfb8/gks672f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/126c/3467067/89f2eb3751b2/gks672f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/126c/3467067/d22d7ff6bd2b/gks672f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/126c/3467067/55cf4cfdea18/gks672f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/126c/3467067/8d9ea214ea19/gks672f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/126c/3467067/fd53eafa12bf/gks672f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/126c/3467067/a5f60ba8bfb8/gks672f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/126c/3467067/89f2eb3751b2/gks672f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/126c/3467067/d22d7ff6bd2b/gks672f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/126c/3467067/55cf4cfdea18/gks672f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/126c/3467067/8d9ea214ea19/gks672f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/126c/3467067/fd53eafa12bf/gks672f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/126c/3467067/a5f60ba8bfb8/gks672f6.jpg

相似文献

1
The solution structure of double helical arabino nucleic acids (ANA and 2'F-ANA): effect of arabinoses in duplex-hairpin interconversion.双螺旋阿拉伯糖核酸（ANA 和 2'F-ANA）的溶液结构：阿拉伯糖在双链发夹互变中的作用。
Nucleic Acids Res. 2012 Oct;40(18):9329-39. doi: 10.1093/nar/gks672. Epub 2012 Jul 14.
2
Duplex recognition by oligonucleotides containing 2'-deoxy-2'-fluoro-D-arabinose and 2'-deoxy-2'-fluoro-D-ribose. Intermolecular 2'-OH-phosphate contacts versus sugar puckering in the stabilization of triple-helical complexes.含2'-脱氧-2'-氟-D-阿拉伯糖和2'-脱氧-2'-氟-D-核糖的寡核苷酸的双链识别。三链螺旋复合物稳定中分子间2'-OH-磷酸接触与糖折叠的关系。
Bioconjug Chem. 1999 Mar-Apr;10(2):299-305. doi: 10.1021/bc9801171.
3
Solution structure of an arabinonucleic acid (ANA)/RNA duplex in a chimeric hairpin: comparison with 2'-fluoro-ANA/RNA and DNA/RNA hybrids.嵌合发夹中阿拉伯核糖核酸（ANA）/RNA双链体的溶液结构：与2'-氟代-ANA/RNA和DNA/RNA杂交体的比较
Nucleic Acids Res. 2001 Nov 1;29(21):4284-93. doi: 10.1093/nar/29.21.4284.
4
Differential stability of 2'F-ANA*RNA and ANA*RNA hybrid duplexes: roles of structure, pseudohydrogen bonding, hydration, ion uptake and flexibility.2'F-ANA*RNA 和 ANA*RNA 杂交双链体的差异稳定性：结构、拟氢键、水合作用、离子摄取和柔韧性的作用。
Nucleic Acids Res. 2010 Apr;38(7):2498-511. doi: 10.1093/nar/gkp1225. Epub 2010 Jan 13.
5
2'-Deoxy-2'-fluoro-beta-D-arabinonucleosides and oligonucleotides (2'F-ANA): synthesis and physicochemical studies.2'-脱氧-2'-氟-β-D-阿拉伯核苷及寡核苷酸（2'F-ANA）：合成与物理化学研究
Nucleic Acids Res. 2000 Sep 15;28(18):3625-35. doi: 10.1093/nar/28.18.3625.
6
2'β-Fluoro-Tricyclo Nucleic Acids (2'F-tc-ANA): Thermal Duplex Stability, Structural Studies, and RNase H Activation.2'β-氟代三环核酸（2'F-tc-ANA）：热双链稳定性、结构研究和 RNase H 激活。
Chemistry. 2017 Aug 1;23(43):10310-10318. doi: 10.1002/chem.201701476. Epub 2017 Jun 13.
7
NMR solution structure of an oligonucleotide hairpin with a 2'F-ANA/RNA stem: implications for RNase H specificity toward DNA/RNA hybrid duplexes.具有2'F-ANA/RNA茎的寡核苷酸发夹的核磁共振溶液结构：对核糖核酸酶H对DNA/RNA杂交双链体特异性的影响
J Am Chem Soc. 2001 May 30;123(21):4896-903. doi: 10.1021/ja003859p.
8
Structural basis of cleavage by RNase H of hybrids of arabinonucleic acids and RNA.阿拉伯核酸与RNA杂交体被核糖核酸酶H切割的结构基础。
Biochemistry. 2000 Apr 4;39(13):3525-32. doi: 10.1021/bi992792j.
9
Studies on the hydrolytic stability of 2'-fluoroarabinonucleic acid (2'F-ANA).2'-氟阿拉伯核酸（2'F-ANA）水解稳定性的研究。
Org Biomol Chem. 2009 May 7;7(9):1904-10. doi: 10.1039/b900443b. Epub 2009 Mar 19.
10
G-quadruplex induced stabilization by 2'-deoxy-2'-fluoro-D-arabinonucleic acids (2'F-ANA).2'-脱氧-2'-氟-D-阿拉伯核酸（2'F-ANA）诱导的G-四链体稳定化
Nucleic Acids Res. 2007;35(15):4977-88. doi: 10.1093/nar/gkm520. Epub 2007 Jul 17.

引用本文的文献

1
The 2'-endo conformation of arabinose-CTP and arabinose-UTP inhibit viral polymerases by inducing long pauses.阿拉伯糖-CTP和阿拉伯糖-UTP的2'-内型构象通过诱导长时间停顿来抑制病毒聚合酶。
bioRxiv. 2025 Aug 26:2025.08.26.672356. doi: 10.1101/2025.08.26.672356.
2
Observing nucleotide flipping in DNA using indirect 2'-F nucleotide probes and 19F NMR.使用间接2'-F核苷酸探针和19F核磁共振观察DNA中的核苷酸翻转。
Nucleic Acids Res. 2025 Jun 6;53(11). doi: 10.1093/nar/gkaf492.
3
Fluorogenic oligonucleotide cleavage probes with a branched linker improve RNA detection.

本文引用的文献

1
Synthetic genetic polymers capable of heredity and evolution.能够遗传和进化的合成遗传聚合物。
Science. 2012 Apr 20;336(6079):341-4. doi: 10.1126/science.1217622.
2
The conformationally constrained N-methanocarba-dT analogue adopts an unexpected C4'-exo sugar pucker in the structure of a DNA hairpin.构象受限的 N-甲撑基-dT 类似物在 DNA 发夹结构中呈现出一种出人意料的 C4'-外式糖环构象。
Biochemistry. 2012 Apr 3;51(13):2639-41. doi: 10.1021/bi300215k. Epub 2012 Mar 20.
3
Dynamic metabolic labeling of DNA in vivo with arabinosyl nucleosides.
带有分支连接子的荧光寡核苷酸切割探针可改善RNA检测。
Nucleic Acids Res. 2025 Feb 27;53(5). doi: 10.1093/nar/gkaf141.
4
Antisense targeting of FOXP3+ Tregs to boost anti-tumor immunity.靶向 FOXP3+Tregs 以增强抗肿瘤免疫。
Front Immunol. 2024 Aug 21;15:1426657. doi: 10.3389/fimmu.2024.1426657. eCollection 2024.
5
Constraints on the emergence of RNA through non-templated primer extension with mixtures of potentially prebiotic nucleotides.通过潜在的前生物核苷酸混合物进行无模板引物延伸对 RNA 出现的限制。
Nucleic Acids Res. 2024 Jun 10;52(10):5451-5464. doi: 10.1093/nar/gkae355.
6
Improving DNA nanostructure stability: A review of the biomedical applications and approaches.提高 DNA 纳米结构稳定性：生物医学应用和方法综述。
Int J Biol Macromol. 2024 Mar;260(Pt 1):129495. doi: 10.1016/j.ijbiomac.2024.129495. Epub 2024 Jan 14.
7
Telomeric i-motifs and C-strands inhibit parallel G-quadruplex extension by telomerase.端粒 i -motifs 和 C 链通过端粒酶抑制平行 G-四链体的延伸。
Nucleic Acids Res. 2023 Oct 27;51(19):10395-10410. doi: 10.1093/nar/gkad764.
8
Nucleic acid nanostructures for applications: The influence of morphology on biological fate.用于应用的核酸纳米结构：形态对生物命运的影响。
Appl Phys Rev. 2023 Mar;10(1):011304. doi: 10.1063/5.0121820.
9
i-Motif folding intermediates with zero-nucleotide loops are trapped by 2'-fluoroarabinocytidine via F···H and O···H hydrogen bonds.具有零核苷酸环的i-基序折叠中间体通过F···H和O···H氢键被2'-氟阿拉伯糖胞苷捕获。
Commun Chem. 2023 Feb 16;6(1):31. doi: 10.1038/s42004-023-00831-7.
10
Promising Advances in Pharmacotherapy for Patients with Spinal Cord Injury-A Review of Studies Performed In Vivo with Modern Drugs.脊髓损伤患者药物治疗的前景进展——对现代药物体内研究的综述
J Clin Med. 2022 Nov 11;11(22):6685. doi: 10.3390/jcm11226685.
体内阿拉伯糖核苷的动态代谢标记 DNA。
Proc Natl Acad Sci U S A. 2011 Dec 20;108(51):20404-9. doi: 10.1073/pnas.1101126108. Epub 2011 Dec 5.
4
Synthesis, improved antisense activity and structural rationale for the divergent RNA affinities of 3'-fluoro hexitol nucleic acid (FHNA and Ara-FHNA) modified oligonucleotides.3'-氟代己糖醇核酸（FHNA 和 Ara-FHNA）修饰寡核苷酸对不同 RNA 亲和力的合成、提高反义活性和结构推理。
J Am Chem Soc. 2011 Oct 19;133(41):16642-9. doi: 10.1021/ja207086x. Epub 2011 Sep 22.
5
Unique gene-silencing and structural properties of 2'-fluoro-modified siRNAs.2'-氟修饰的小干扰RNA的独特基因沉默和结构特性。
Angew Chem Int Ed Engl. 2011 Mar 1;50(10):2284-8. doi: 10.1002/anie.201006519. Epub 2011 Jan 31.
6
Unexpected origins of the enhanced pairing affinity of 2'-fluoro-modified RNA.2'-氟修饰 RNA 增强配对亲和力的意外起源。
Nucleic Acids Res. 2011 Apr;39(8):3482-95. doi: 10.1093/nar/gkq1270. Epub 2010 Dec 22.
7
Energetically important C-H···F-C pseudohydrogen bonding in water: evidence and application to rational design of oligonucleotides with high binding affinity.在水中具有重要能量意义的 C-H···F-C 假氢键：证据与用于具有高结合亲和力的寡核苷酸的合理设计。
J Am Chem Soc. 2011 Feb 2;133(4):728-31. doi: 10.1021/ja109817p. Epub 2010 Dec 20.
8
Intermolecular C-F...H-C contacts in the molecular packing of three isostructural N-(fluorophenyl)mannopyranosylamines.三种同构的N-（氟苯基）甘露吡喃糖胺分子堆积中的分子间C-F...H-C接触
Acta Crystallogr C. 2010 Dec;66(Pt 12):o565-70. doi: 10.1107/S0108270110043556. Epub 2010 Nov 6.
9
Synergistic effects between analogs of DNA and RNA improve the potency of siRNA-mediated gene silencing.DNA 和 RNA 的类似物之间的协同作用提高了 siRNA 介导的基因沉默的效力。
Nucleic Acids Res. 2010 Jul;38(13):4547-57. doi: 10.1093/nar/gkq181. Epub 2010 Apr 22.
10
Differential stability of 2'F-ANA*RNA and ANA*RNA hybrid duplexes: roles of structure, pseudohydrogen bonding, hydration, ion uptake and flexibility.2'F-ANA*RNA 和 ANA*RNA 杂交双链体的差异稳定性：结构、拟氢键、水合作用、离子摄取和柔韧性的作用。
Nucleic Acids Res. 2010 Apr;38(7):2498-511. doi: 10.1093/nar/gkp1225. Epub 2010 Jan 13.