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

Citation
J. Wang et al., Cyclohexene nucleic acids (CeNA): Serum stable oligonucleotides that activate RNase H and increase duplex stability with complementary RNA, J AM CHEM S, 122(36), 2000, pp. 8595-8602
Citations number
34
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN journal
0002-7863 → ACNP
Volume
122
Issue
36
Year of publication
2000
Pages
8595 - 8602
Database
ISI
SICI code
0002-7863(20000913)122:36<8595:CNA(SS>2.0.ZU;2-1
Abstract
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 b e obtained by the classical phosphoramidite chemisty starting from protecte d cyclohexenyl nucleoside building blocks. Incorporation of cylcohexenyl nu cleosides in a DNA chain increases the stability of a DNA/RNA hybrid. The c omplex formed between cyclohexenyl oligoadenylate and its DNA or RNA comple ment is of similar stability. Circular dichroism (CD) and NMR studies indic ate easy conformational adaptation of a cyclohexenyl nucleoside when incorp orated in a natural nucleic acid structure. CeNA is stable against degradat ion in serum and a CeNA/RNA hybrid is able to activate E. Coli RNase H, res ulting in cleavage of the RNA strand.