期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 7, 页码 2845-2854出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405840
关键词
azobenzenes; nucleic acids; photoisomerization; photoswitches; RNA
资金
- Deutsche Forschungsgemeinschaft (DFG) [SFB 902, EXC 115]
- MEXT of Japan [245431, 25248037, 24104005]
- Grants-in-Aid for Scientific Research [24104005, 25248037, 12J05431] Funding Source: KAKEN
Photoregulation of RNA remains a challenging task as the introduction of a photoswitch entails changes in the shape and the stability of the duplex that strongly depend on the chosen linker strategy. Herein, the influence of a novel nucleosidic linker moiety on the photoregulation efficiency of azobenzene is investigated. To this purpose, two azobenzene C-nucleosides were stereoselectively synthesized, characterized, and incorporated into RNA oligonucleotides. Spectroscopic characterization revealed a reversible and fast switching process, even at 20 degrees C, and a high thermal stability of the respective cis isomers. The photoregulation efficiency of RNA duplexes upon trans-to-cis isomerization was investigated by using melting point studies and compared with the known D-threoninol-based azobenzene system, revealing a photoswitching amplitude of the new residues exceeding 90% even at room temperature. Structural changes in the duplexes upon photoisomerization were investigated by using MM/MD calculations. The excellent photoswitching performance at room temperature and the high thermal stability make these new azobenzene residues promising candidates for in-vivo and nanoarchitecture photoregulation applications of RNA.
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