N(2)-修饰的 2-氨基嘌呤核苷作为双链 RNA 中小沟调节的腺嘌呤替代物。
N(2)-Modified 2-aminopurine ribonucleosides as minor-groove-modulating adenosine replacements in duplex RNA.
机构信息
Department of Chemistry, University of California, Davis, California 95616, USA.
出版信息
Org Lett. 2010 Mar 5;12(5):1044-7. doi: 10.1021/ol100019r.
Abstract
Nucleoside analogs that project substituents into the minor groove when incorporated into duplex RNA perturb the binding of proteins and can affect base pairing specificity. The synthesis of 2-aminopurine ribonucleoside analogs and their phosphoramidites, their incorporation into duplex RNA, their postsynthetic modification via Cu-catalyzed azide-alkyne cycloaddition (CuAAC), and their effect on duplex stability and base pairing specificity are described.
摘要
核苷类似物在整合到双链 RNA 中时会将取代基投射到小沟中，从而扰乱蛋白质的结合，并可能影响碱基配对特异性。本文描述了 2-氨基嘌呤核糖核苷类似物及其磷酰胺的合成、在双链 RNA 中的整合、通过 Cu 催化的叠氮-炔环加成（CuAAC）进行的后期修饰以及它们对双链稳定性和碱基配对特异性的影响。
相似文献
1
N(2)-Modified 2-aminopurine ribonucleosides as minor-groove-modulating adenosine replacements in duplex RNA.N(2)-修饰的 2-氨基嘌呤核苷作为双链 RNA 中小沟调节的腺嘌呤替代物。
Org Lett. 2010 Mar 5;12(5):1044-7. doi: 10.1021/ol100019r.
2
7-Substituted 8-aza-7-deazaadenosines for modification of the siRNA major groove.7-取代 8-氮杂-7-脱氮腺苷用于修饰 siRNA 的大沟。
Org Biomol Chem. 2012 Aug 28;10(32):6491-7. doi: 10.1039/c2ob25647a. Epub 2012 Jul 5.
3
Flexible Alkyne-Linked Thymidine Phosphoramidites and Triphosphates for Chemical or Polymerase Synthesis and Fast Postsynthetic DNA Functionalization through Copper-Catalyzed Alkyne-Azide 1,3-Dipolar Cycloaddition.用于化学或聚合酶合成的柔性炔键连接的胸苷磷酸酰胺和三磷酸酯，以及通过铜催化的炔烃-叠氮化物 1,3-偶极环加成进行快速的后续 DNA 功能化。
Org Lett. 2018 Jul 6;20(13):3962-3965. doi: 10.1021/acs.orglett.8b01533. Epub 2018 Jun 13.
4
Synthesis of novel nucleoside 5'-triphosphates and phosphoramidites containing alkyne or amino groups for the postsynthetic functionalization of nucleic acids.用于核酸合成后功能化的含炔基或氨基的新型核苷5'-三磷酸酯和亚磷酰胺的合成。
Nucleosides Nucleotides Nucleic Acids. 2011 Oct;30(10):753-67. doi: 10.1080/15257770.2011.595379.
5
Structural Determinants of Alkyne Reactivity in Copper-Catalyzed Azide-Alkyne Cycloadditions.铜催化叠氮化物-炔烃环加成反应中炔烃反应性的结构决定因素
Molecules. 2016 Dec 9;21(12):1697. doi: 10.3390/molecules21121697.
6
Efficient RNA-targeting by the introduction of aromatic stacking in the duplex major groove via 5-(1-phenyl-1,2,3-triazol-4-yl)-2'-deoxyuridines.通过在双链体大沟中引入芳族堆积作用，用 5-(1-苯基-1,2,3-三唑-4-基)-2'-脱氧尿苷实现高效的 RNA 靶向。
Bioorg Med Chem. 2010 Jul 1;18(13):4702-10. doi: 10.1016/j.bmc.2010.05.019. Epub 2010 May 12.
7
The CuAAC: Principles, Homogeneous and Heterogeneous Catalysts, and Novel Developments and Applications.铜催化的三组分偶联反应：原理、均相及多相催化剂，以及新的发展与应用。
Macromol Rapid Commun. 2020 Jan;41(1):e1900359. doi: 10.1002/marc.201900359. Epub 2019 Oct 21.
8
Postsynthetic DNA modification through the copper-catalyzed azide-alkyne cycloaddition reaction.通过铜催化的叠氮化物-炔烃环加成反应进行的合成后DNA修饰。
Angew Chem Int Ed Engl. 2008;47(44):8350-8. doi: 10.1002/anie.200802077.
9
Optimized Methods for the Production and Bioconjugation of Site-Specific, Alkyne-Modified Glucagon-like Peptide-1 (GLP-1) Analogs to Azide-Modified Delivery Platforms Using Copper-Catalyzed Alkyne-Azide Cycloaddition.使用铜催化的炔基-叠氮化物环加成反应将位点特异性、炔基修饰的胰高血糖素样肽-1（GLP-1）类似物与叠氮化物修饰的递送平台进行生产和生物共轭的优化方法。
Bioconjug Chem. 2020 Jul 15;31(7):1820-1834. doi: 10.1021/acs.bioconjchem.0c00291. Epub 2020 Jun 25.
10
Quick and highly efficient copper-catalyzed cycloaddition of organic azides with terminal alkynes.快速高效的铜催化末端炔烃与有机叠氮化物的环加成反应。
Org Biomol Chem. 2012 Jan 14;10(2):229-31. doi: 10.1039/c1ob06190a. Epub 2011 Oct 24.
引用本文的文献
1
Synthesis of Nucleobase-Modified RNA Oligonucleotides by Post-Synthetic Approach.通过后期合成方法合成碱基修饰的 RNA 寡核苷酸。
Molecules. 2020 Jul 23;25(15):3344. doi: 10.3390/molecules25153344.
2
Practical synthesis of -(di--butylamino)methylene-protected 2-aminopurine riboside phosphoramidite for RNA solid-phase synthesis.用于RNA固相合成的-(二-叔丁基氨基)亚甲基保护的2-氨基嘌呤核糖核苷亚磷酰胺的实用合成。
Monatsh Chem. 2019;150(11):1941-1946. doi: 10.1007/s00706-019-02502-7. Epub 2019 Oct 11.
3
Targeting Base Excision Repair Glycosylases with DNA Containing Transition State Mimics Prepared via Click Chemistry.通过点击化学制备含有过渡态模拟物的 DNA 靶向碱基切除修复糖苷酶。
ACS Chem Biol. 2019 Jan 18;14(1):27-36. doi: 10.1021/acschembio.8b00771. Epub 2019 Jan 2.
4
TLR8 activation and inhibition by guanosine analogs in RNA: Importance of functional groups and chain length.鸟苷类似物在RNA中对Toll样受体8（TLR8）的激活和抑制作用：官能团和链长的重要性
Bioorg Med Chem. 2018 Jan 1;26(1):77-83. doi: 10.1016/j.bmc.2017.11.020. Epub 2017 Nov 11.
5
Structures of human ADAR2 bound to dsRNA reveal base-flipping mechanism and basis for site selectivity.与双链RNA结合的人类ADAR2的结构揭示了碱基翻转机制和位点选择性的基础。
Nat Struct Mol Biol. 2016 May;23(5):426-33. doi: 10.1038/nsmb.3203. Epub 2016 Apr 11.
6
Synthesis and evaluation of an alkyne-modified ATP analog for enzymatic incorporation into RNA.一种用于酶促掺入RNA的炔烃修饰ATP类似物的合成与评价。
Bioorg Med Chem Lett. 2016 Apr 1;26(7):1799-802. doi: 10.1016/j.bmcl.2016.02.038. Epub 2016 Feb 18.
7
Recognition of duplex RNA by the deaminase domain of the RNA editing enzyme ADAR2.RNA编辑酶ADAR2的脱氨酶结构域对双链RNA的识别。
Nucleic Acids Res. 2015 Jan;43(2):1123-32. doi: 10.1093/nar/gku1345. Epub 2015 Jan 6.
8
Base modification strategies to modulate immune stimulation by an siRNA.通过小干扰RNA（siRNA）调节免疫刺激的碱基修饰策略。
Chembiochem. 2015 Jan 19;16(2):262-7. doi: 10.1002/cbic.201402551. Epub 2014 Dec 8.
9
Click modification of RNA at adenosine: structure and reactivity of 7-ethynyl- and 7-triazolyl-8-aza-7-deazaadenosine in RNA.RNA中腺苷的点击修饰：RNA中7-乙炔基和7-三唑基-8-氮杂-7-脱氮腺苷的结构与反应活性
ACS Chem Biol. 2014 Aug 15;9(8):1780-7. doi: 10.1021/cb500270x. Epub 2014 Jun 16.
10
Short interfering RNA guide strand modifiers from computational screening.短干扰 RNA 引导链修饰物的计算筛选。
J Am Chem Soc. 2013 Nov 13;135(45):17069-77. doi: 10.1021/ja4079754. Epub 2013 Nov 5.
本文引用的文献
1
2'-amino-modified ribonucleotides as probes for local interactions within RNA.
Methods Enzymol. 2009;468:107-25. doi: 10.1016/S0076-6879(09)68006-X. Epub 2009 Nov 17.
2
Small molecule induced control in duplex and triplex DNA-directed chemical reactions.小分子诱导的双链和三链 DNA 导向的化学反应控制。
Org Biomol Chem. 2010 Jan 7;8(1):50-2. doi: 10.1039/b919387a. Epub 2009 Nov 9.
3
RNA major groove modifications improve siRNA stability and biological activity.RNA大沟修饰可提高小干扰RNA（siRNA）的稳定性和生物学活性。
Nucleic Acids Res. 2009 Feb;37(2):346-53. doi: 10.1093/nar/gkn958. Epub 2008 Nov 28.
4
Fluorine substituted adenosines as probes of nucleobase protonation in functional RNAs.氟取代腺苷作为功能性RNA中核碱基质子化的探针。
J Am Chem Soc. 2008 Oct 15;130(41):13639-48. doi: 10.1021/ja803336y. Epub 2008 Sep 20.
5
Combinatorial chemoenzymatic synthesis and high-throughput screening of sialosides.唾液酸苷的组合化学酶法合成与高通量筛选
ACS Chem Biol. 2008 Sep 19;3(9):567-76. doi: 10.1021/cb800127n. Epub 2008 Aug 27.
6
Cu-catalyzed azide-alkyne cycloaddition.铜催化的叠氮化物-炔烃环加成反应
Chem Rev. 2008 Aug;108(8):2952-3015. doi: 10.1021/cr0783479.
7
Chemically modified siRNA: tools and applications.化学修饰的小干扰RNA：工具与应用
Drug Discov Today. 2008 Oct;13(19-20):842-55. doi: 10.1016/j.drudis.2008.05.007. Epub 2008 Jul 7.
8
Small interfering RNAs induce macrophage migration inhibitory factor production and proliferation in breast cancer cells via a double-stranded RNA-dependent protein kinase-dependent mechanism.小干扰RNA通过双链RNA依赖性蛋白激酶依赖性机制诱导乳腺癌细胞产生巨噬细胞迁移抑制因子并促进其增殖。
J Immunol. 2008 Jun 1;180(11):7125-33. doi: 10.4049/jimmunol.180.11.7125.
9
Rapid and efficient DNA strand cross-linking by click chemistry.通过点击化学实现快速高效的DNA链交联
Chembiochem. 2008 May 23;9(8):1280-5. doi: 10.1002/cbic.200800006.
10
Probing adenosine-to-inosine editing reactions using RNA-containing nucleoside analogs.使用含RNA的核苷类似物探究腺苷到肌苷的编辑反应。
Methods Enzymol. 2007;424:369-86. doi: 10.1016/S0076-6879(07)24017-0.
Zotero 插件