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Efficient Synthesis of Ratiometric Fluorescent Nucleosides Featuring 3-Hydroxychromone Nucleobases |
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| Authors: | Marie Spadafora Volodymyr V Shvadchak Yves Mély Rachid Benhida |
| Institution: | a Laboratoire de Chimie des Molécules Bioactives et des Arômes, UMR 6001 CNRS, Institut de Chimie de Nice, Université de Nice-Sophia Antipolis, Parc Valrose, 06108 Nice Cedex 2, France b Laboratoire de Biophotonique et Pharmacologie, UMR 7213 CNRS, Université de Strasbourg, Faculté de Pharmacie 74, Route du Rhin, BP 24, 67401 Illkirch cedex, France |
| Abstract: | The synthesis of a novel class of fluorescent nucleosides featuring 2-aryl-3-hydroxychromones (3-HC) as base analogues is described. Nucleoside 1a bearing the 2-thienyl-3-HC nucleobase was prepared using sequential aryl-aldol condensation/cycloetherification or a Friedel-Crafts glycosylation as key steps. The synthesis of the triazolyl derivative 1b was achieved using a convergent 1,3-dipolar cycloaddition strategy. Fluorescence studies show that 3-HC-thienyl-nucleoside 1a displays high sensitivity of its dual emission to polarity changes and therefore is highly promising for nucleic acid labelling. |
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