Cyclohexene nucleic acids (CeNA): Serum stable oligonucleotides that activate RNase H and increase duplex stability with complementary RNA

Autor(en): Wang, J
Verbeure, B
Luyten, I
Lescrinier, E
Froeyen, M
Hendrix, C
Rosemeyer, H 
Seela, F
Van Aerschot, A
Herdewijn, P
Stichwörter: Chemistry; Chemistry, Multidisciplinary; DNA; HYBRIDS; NMR-SPECTROSCOPY; NUCLEOSIDES
Erscheinungsdatum: 2000
Herausgeber: AMER CHEMICAL SOC
Journal: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volumen: 122
Ausgabe: 36
Startseite: 8595
Seitenende: 8602
Zusammenfassung: 
The replacement of the furanose moiety of DNA by a cyclohexene ring gives a new nucleic acid structure: cyclohexene nucleic acids or CeNA. CeNAs can be obtained by the classical phosphoramidite chemisty starting from protected cyclohexenyl nucleoside building blocks. Incorporation of cylcohexenyl nucleosides in a DNA chain increases the stability of a DNA/RNA hybrid. The complex formed between cyclohexenyl oligoadenylate and its DNA or RNA complement is of similar stability. Circular dichroism (CD) and NMR studies indicate easy conformational adaptation of a cyclohexenyl nucleoside when incorporated in a natural nucleic acid structure. CeNA is stable against degradation in serum and a CeNA/RNA hybrid is able to activate E. Coli RNase H, resulting in cleavage of the RNA strand.
ISSN: 00027863
DOI: 10.1021/ja000018+

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