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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geprüft am 21.05.2024