Analogues of a locked nucleic acid with three-carbon 2',4'-linkages: synthesis by ring-closing metathesis and influence on nucleic acid duplex stability and structure.
J Org Chem
; 71(20): 7731-40, 2006 Sep 29.
Article
en En
| MEDLINE
| ID: mdl-16995680
ABSTRACT
Two bicyclic 2'-deoxynucleoside analogues containing a saturated and an unsaturated three-carbon 2',4'-linkage, respectively, have been synthesized using a ring-closing metathesis-based linear strategy starting from uridine. Both analogues have been incorporated into oligodeoxynucleotide sequences and increased the stability of DNARNA hybrid duplexes (DeltaT(m) approximately 2.5-5.0 degrees C per modification) and decreased the stability of dsDNA duplexes (DeltaT(m) approximately 2.5-1.0 degrees C per modification). CD spectroscopy revealed that the bicyclic nucleosides induced formation of A-type-like duplexes albeit to a lesser degree than found for locked nucleic acid (LNA) monomers. From the CD data and UV melting analysis, we propose that the 2'-oxygen atom of the bicyclic moiety is essential for the formation of stabilized A-type-like dsDNA but not for the formation of a stabilized A-type DNARNA hybrid.
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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
ADN
/
ARN
/
Oligonucleótidos Antisentido
Idioma:
En
Revista:
J Org Chem
Año:
2006
Tipo del documento:
Article
País de afiliación:
Dinamarca