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Hernandez Lladó Pol.pdf (2.69 MB)

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Bachelor thesis

Publication date

2017-06

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cc-by-nc-nd (c) Hernàndez, 2017
Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/116060

Asymmetric organocatalytic synthesis of dinucleoside phosphorothioates. Towards antisense therapy

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Abstract

Phosphorothioate oligonucleotides have been deeply studied as antisense therapy drugs. Their stereoselective synthesis, however, still depends on the use of chiral auxiliaries or modifications on the individual nucleosides, which slow their synthesis and increase costs. A catalytic asymmetric synthesis of these oligonucleotides would therefore be of great interest. Herein the catalytic asymmetric synthesis of dinucleoside phosphorothioates is attempted. After failing to optimise the conditions for the coupling using 4-DMAP-N-oxides as nucleophilic catalysts, hydrogen bond donors were envisaged as potential catalysts. Through the use of bifunctional thioureas containing a tethered amine, adequate conditions for the coupling were found and diastereoselectivity could be measured. Although low conversions were obtained, moderate selectivities were achieved for the synthesis of these dinucleosides

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Treballs Finals de Grau de Química, Facultat de Química, Universitat de Barcelona, Any: 2017, Tutors: Alan C. Spivey, Fèlix Urpí

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Nucleòtids, Compostos orgànics, Catàlisi asimètrica, Treballs de fi de grau

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Nucleotides, Organic compounds, Enantioselective catalysis, Bachelor's theses

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Treballs Finals de Grau (TFG) - Química

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HERNÁNDEZ LLADÓ, Pol. Asymmetric organocatalytic synthesis of dinucleoside phosphorothioates. Towards antisense therapy. [consulted: 7 of August of 2026]. Available at: https://hdl.handle.net/2445/116060

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