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Synthesis of Janus compounds for the recognition of G-U mismatched nucleobase pairs
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The design and synthesis of two Janus-type heterocycles with the capacity to simultaneously recognize guanine and uracyl in G-U mismatched pairs through complementary hydrogen bond pairing is described. Both compounds were conveniently functionalized with a carboxylic function and efficiently attached to a tripeptide sequence by using solid-phase methodologies. Ligands based on the derivatization of such Janus compounds with a small aminoglycoside, neamine, and its guanidinylated analogue have been synthesized, and their interaction with Tau RNA has been investigated by using several biophysical techniques, including UV-monitored melting curves, fluorescence titration experiments, and 1H NMR. The overall results indicated that Janus-neamine/guanidinoneamine showed some preference for the +3 mutated RNA sequence associated with the development of some tauopathies, although preliminary NMR studies have not confirmed binding to G-U pairs. Moreover, a good correlation has been found between the RNA binding affinity of such Janus-containing ligands and their ability to stabilize this secondary structure upon complexation.
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ARTIGAS SOLÉ, Gerard and MARCHÁN SANCHO, Vicente. Synthesis of Janus compounds for the recognition of G-U mismatched nucleobase pairs. Journal of Organic Chemistry. 2013. Vol. 78, num. 21, pags. 10666-10677. ISSN 0022-3263. [consulted: 22 of June of 2026]. Available at: https://hdl.handle.net/2445/48338