Novel conformationally locked nucleosides and nucleotides

0428926 - ÚOCHB 2015 CZ eng C - Konferenční příspěvek (zahraniční konf.)
Nencka, Radim - Šála, Michal - Hřebabecký, Hubert - Procházková, Eliška - Mackman, R. - Barauskas, O. - Lee, Y. J. - Tian, Y.
Novel conformationally locked nucleosides and nucleotides.
Chemistry of Nucleic Acid Components. 16th Symposium. Praha: Institute of Organic Chemistry and Biochemistry AS CR, v. v. i, 2014 - (Hocek, M.), s. 119-122. Collection Symposium Series, 14. ISBN 978-80-86241-50-0.
[Symposium on Chemistry of Nucleic Acid Components /16./. Český Krumlov (CZ), 08.06.2014-13.06.2014]
Grant CEP: GA ČR GPP207/12/P625; GA MV VG20102015046
Institucionální podpora: RVO:61388963
Klíčová slova: locked nucleoside analogues * oligonucleotide synthesis
Kód oboru RIV: CC - Organická chemie

We report on a synthesis of two novel types of conformationally locked nucleoside analogues. We prepared 7 membered ring 3’,5’-bridged nucleoside analogs locked in a Southern conformation. These nucleoside analogues were converted in one pot to appropriate phosphoramidate prodrugs using boronate methodology. We also devised and prepared a novel carbocyclic nucleoside by replacing furanose with cyclohexene that resulted in a locked Northern conformation similar to LNA monomers. Further details on the biological activity and application for oligonucleotide synthesis will be discussed in detail.
Trvalý link: http://hdl.handle.net/11104/0234281