title: Synthesis of locked cyclohexene and cyclohexane nucleic acids (LCeNA and LCNA) with modified adenosine units.
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.
authors.affiliation: Gilead Sciences & IOCB Research Centre, Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, v.v.i. Flemingovo n. 2, 16610, Prague, Czech Republic. sala@uochb.cas.cz nencka@uochb.cas.cz.
authors.forename: Michal
authors.initials: M
authors.lastname: Šála
authors.forename: Milan
authors.initials: M
authors.lastname: Dejmek
authors.forename: Eliška
authors.initials: E
authors.lastname: Procházková
authors.forename: Hubert
authors.initials: H
authors.lastname: Hřebabecký
authors.forename: Jiří
authors.initials: J
authors.lastname: Rybáček
authors.forename: Martin
authors.initials: M
authors.lastname: Dračínský
authors.forename: Pavel
authors.initials: P
authors.lastname: Novák
authors.forename: Šárka
authors.initials: Š
authors.lastname: Rosenbergová
authors.forename: Jiří
authors.initials: J
authors.lastname: Fukal
authors.forename: Vladimír
authors.initials: V
authors.lastname: Sychrovský
authors.forename: Ivan
authors.initials: I
authors.lastname: Rosenberg
authors.forename: Radim
authors.initials: R
authors.lastname: Nencka
mesh_terms: D000241:Adenosine / Q000138:chemical synthesis / Q000737:chemistry*; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009696:Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D003510:Cyclohexanes; D009696:Nucleic Acids; C506365:Cyclohexane; D000241:Adenosine