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Synthesis of locked cyclohexene and cyclohexane nucleic acids (LCeNA and LCNA) with modified adenosine units†
Michal Šála,Milan Dejmek,Eliška Procházková,Hubert Hřebabecký,Jiří Rybáček,Martin Dračínský,Pavel Novák,Šárka Rosenbergová,Jiří Fukal,Vladimír Sychrovský,Ivan Rosenberg,Radim Nencka
Organic & Biomolecular Chemistry Pub Date : 01/02/2015 00:00:00 , DOI:10.1039/C4OB02193B
Abstract

We describe here the preparation of conformationally locked cyclohexane nucleic acids designed as hybrids between locked nucleic acids (LNAs) and cyclohexene nucleic acids (CeNAs), both of which excel in hybridization with complementary RNAs. We have accomplished the synthesis of these adenine derivatives starting from a simple ketoester and installed all four chiral centres by means of total synthesis. The acquired monomers were incorporated into nonamer oligonucleotides.

Graphical abstract: Synthesis of locked cyclohexene and cyclohexane nucleic acids (LCeNA and LCNA) with modified adenosine units
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