Synthesis 2015; 47(17): 2654-2662
DOI: 10.1055/s-0034-1380744
paper
© Georg Thieme Verlag Stuttgart · New York

A New Analogue of Locked Cyclohexane Nucleic Acids

Michal Šála*
Gilead Sciences and 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   Email: sala@uochb.cas.cz   Email: nencka@uochb.cas.cz
,
Milan Dejmek
Gilead Sciences and 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   Email: sala@uochb.cas.cz   Email: nencka@uochb.cas.cz
,
Eliška Procházková
Gilead Sciences and 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   Email: sala@uochb.cas.cz   Email: nencka@uochb.cas.cz
,
Hubert Hřebabecký
Gilead Sciences and 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   Email: sala@uochb.cas.cz   Email: nencka@uochb.cas.cz
,
Jiří Rybáček
Gilead Sciences and 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   Email: sala@uochb.cas.cz   Email: nencka@uochb.cas.cz
,
Martin Dračínský
Gilead Sciences and 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   Email: sala@uochb.cas.cz   Email: nencka@uochb.cas.cz
,
Pavel Novák
Gilead Sciences and 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   Email: sala@uochb.cas.cz   Email: nencka@uochb.cas.cz
,
Šárka Rosenbergová
Gilead Sciences and 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   Email: sala@uochb.cas.cz   Email: nencka@uochb.cas.cz
,
Ivan Rosenberg
Gilead Sciences and 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   Email: sala@uochb.cas.cz   Email: nencka@uochb.cas.cz
,
Radim Nencka*
Gilead Sciences and 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   Email: sala@uochb.cas.cz   Email: nencka@uochb.cas.cz
› Author Affiliations
Further Information

Publication History

Received: 11 January 2015

Accepted after revision: 16 April 2015

Publication Date:
28 May 2015 (online)


Abstract

We report on a new analogue of locked cyclohexane nucleic acids that contains an adenine nucleobase at an alternative position and which resembles homo-DNA. The crucial locked carbocyclic nucleo­side monomer was prepared with high enantioselectivity and was subsequently incorporated into a pair of modified oligonucleotides that were subjected to hybridization studies.

Supporting Information