发光 RNA 字母表。
Emissive RNA alphabet.
机构信息
Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093-0358, United States.
出版信息
J Am Chem Soc. 2011 Sep 28;133(38):14912-5. doi: 10.1021/ja206095a. Epub 2011 Sep 2.
Abstract
A fluorescent ribonucleoside alphabet consisting of highly emissive purine ((th)A, (th)G) and pyrimidine ((th)U, (th)C) analogues, all derived from thieno[3,4-d]pyrimidine as the heterocyclic nucleus, is described. Structural and biophysical analyses demonstrated that the emissive analogues are faithful isomorphic nucleoside surrogates. Photophysical analysis established that the nucleosides offer highly desirable qualities, including visible emission, high quantum yield, and responsiveness to environmental perturbations, traits entirely lacking in their native counterparts.
摘要
一个由高度发光的嘌呤（（th）A、（th）G）和嘧啶（（th）U、（th）C）类似物组成的荧光核苷字母表被描述，所有的类似物都源自噻吩[3,4-d]嘧啶作为杂环核。结构和生物物理分析表明，发光类似物是忠实的同构核苷替代物。光物理分析确定了这些核苷具有高度理想的特性，包括可见发射、高量子产率和对环境扰动的响应性，而这些特性在其天然对应物中完全缺失。
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1
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2
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Expert Rev Mol Diagn. 2011 Apr;11(3):321-31. doi: 10.1586/erm.11.5.
3
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Chemphyschem. 2011 Feb 25;12(3):567-70. doi: 10.1002/cphc.201001002. Epub 2010 Dec 27.
4
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Nucleic Acids Res. 2011 May;39(10):4513-24. doi: 10.1093/nar/gkr010. Epub 2011 Jan 29.
5
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Org Lett. 2011 Feb 18;13(4):676-9. doi: 10.1021/ol102915f. Epub 2011 Jan 7.
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7
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