期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 28, 页码 7974-7978出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201601688
关键词
ab initio calculations; fluorescence; molecular modeling; nucleic acids; tautomerism
资金
- Ministere de la Recherche
- European Project THINPAD Targeting the HIV-1 Nucleocapsid Protein to fight Antiretroviral Drug Resistance [601969]
- Agence Nationale de la Recherche (ANR blanc Fluometadn)
- Agence Nationale de la Recherche (ANR FEMTOSTACK)
- Agence Nationale de Recherche sur le SIDA
- French-Ukrainian Dnipro program
- Universite de Strasbourg
- Centre National de la Recherche Scientifique (CNRS)
- Institut de la Sante et de la Recherche Medicale (INSERM)
- Progetto Bilaterale CNR/CNRS
- US National Institutes of Health [GM 069773]
- EQUIP@MESO
Thienoguanosine ((th)G) is an isomorphic nucleoside analogue acting as a faithful fluorescent substitute of G, with respectable quantum yield in oligonucleotides. Photophysical analysis of (th)G reveals the existence of two ground-state tautomers with significantly shifted absorption and emission wavelengths, and high quantum yield in buffer. Using (TD)-DFT calculations, the tautomers were identified as the H1 and H3 keto-amino tautomers. When incorporated into the loop of (-) PBS, the (-) DNA copy of the HIV-1 primer binding site, both tautomers are observed and show differential sensitivity to protein binding. The red-shifted H1 tautomer is strongly favored in matched (-)/(+) PBS duplexes, while the relative emission of the H3 tautomer can be used to detect single nucleotide polymorphisms. These tautomers and their distinct environmental sensitivity provide unprecedented information channels for analyzing G residues in oligonucleotides and their complexes.
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