Anti Regiospecificity in the Photosensitized Cycloaddition of 4‐Tetrazolouracil Nucleoside †
| Autor: | Frédéric Peyrane, Clément Denhez, Dominique Guillaume, Pascale Clivio |
|---|---|
| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Pyrimidine
Stereochemistry Ultraviolet Rays education 010402 general chemistry 01 natural sciences Biochemistry Nucleobase chemistry.chemical_compound Isomerism Acetone Physical and Theoretical Chemistry Cycloaddition Reaction 010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Regioselectivity Nucleosides General Medicine Cycloaddition 3. Good health 0104 chemical sciences chemistry Pyrimidine Dimers Yield (chemistry) [CHIM.OTHE]Chemical Sciences/Other Nucleoside Cyclobutanes |
| Zdroj: | Photochemistry and Photobiology Photochemistry and Photobiology, Wiley, 2021, ⟨10.1111/php.13541⟩ |
| ISSN: | 0031-8655 |
| DOI: | 10.1111/php.13541⟩ |
| Popis: | International audience; The [2 + 2] photocycloaddition of natural pyrimidine nucleobases is devoid of regioselectivity. Although modified pyrimidines have been developed to selectively obtain syn-cyclobutane isomers, the targeted formation of anti-cyclobutane isomers has not been addressed yet. Herein, using NMR analyses and DFT calculations, we demonstrate that the acetone photosensitized excitation of the 4-tetrazolouracil motif in the nucleoside series specifically provides anti-cyclobutane photoproducts in 51% yield. In addition, the cis stereomer formation is preferred over the trans-cyclobutane formation (71:29). |
| Databáze: | OpenAIRE |
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