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- Title
Hybridization Properties of RNA Containing 8-Methoxyguanosine and 8-Benzyloxyguanosine.
- Authors
Baranowski, Daniel Sylwester; Kotkowiak, Weronika; Kierzek, Ryszard; Pasternak, Anna
- Abstract
Modified nucleobase analogues can serve as powerful tools for changing physicochemical and biological properties of DNA or RNA. Guanosine derivatives containing bulky substituents at 8 position are known to adopt syn conformation of N-glycoside bond. On the contrary, in RNA the anti conformation is predominant in Watson-Crick base pairing. In this paper two 8-substituted guanosine derivatives, 8-methoxyguanosine and 8-benzyloxyguanosine, were synthesized and incorporated into oligoribonucleotides to investigate their influence on the thermodynamic stability of RNA duplexes. The methoxy and benzyloxy substituents are electron-donating groups, decreasing the rate of depurination in the monomers, as confirmed by N-glycoside bond stability assessments. Thermodynamic stability studies indicated that substitution of guanosine by 8-methoxy- or 8-benzyloxyguanosine significantly decreased the thermodynamic stability of RNA duplexes. Moreover, the presence of 8-substituted guanosine derivatives decreased mismatch discrimination. Circular dichroism spectra of modified RNA duplexes exhibited patterns typical for A-RNA geometry.
- Subjects
RNA analysis; GUANOSINE derivatives; BASE pairs; GLYCOSIDES; SUBSTITUENTS (Chemistry); THERMODYNAMICS
- Publication
PLoS ONE, 2015, Vol 10, Issue 9, p1
- ISSN
1932-6203
- Publication type
Article
- DOI
10.1371/journal.pone.0137674