Synthesis and hybridization properties of modified oligodeoxynucleotides carrying non-natural bases

The impact of the presence of nonnatural bases on the properties of oligodeoxynucleotides has been studied. First, oligodeoxynucleotides carrying 2′-deoxyzebularine were prepared, and the stability of duplexes carrying this analogue was determined by DNAmelting experiments. Melting temperatures and...

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Detalles Bibliográficos
Autores: Aviñó, Anna, Pérez-Rentero, Sonia, Garibotti, Alejandra V., Siddiqui, Maqbool Arshad Q, Márquez, Víctor E., Eritja Casadellà, Ramón
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2009
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/125042
Acceso en línea:http://hdl.handle.net/10261/125042
Access Level:acceso abierto
Palabra clave:Base pairing
Base sequence
Cytidine
DNA
Nucleic Acid Conformation
Nucleic Acid Denaturation
Nucleic Acid Hybridization
Oligodeoxyribonucleotides
Thermodynamics
unclassified drug
zebularine
Descripción
Sumario:The impact of the presence of nonnatural bases on the properties of oligodeoxynucleotides has been studied. First, oligodeoxynucleotides carrying 2′-deoxyzebularine were prepared, and the stability of duplexes carrying this analogue was determined by DNAmelting experiments. Melting temperatures and thermodynamic data indicated the preference of 2′-deoxyzebularine for 2′-deoxyguanosine, which behaves as a 2′-deoxycytidine analogue, forming a less stable base pair due to the absence of the amino group at position 4. Moreover, the duplex - hairpin equilibrium of a self-complementary oligodeoxynucleotide carrying several natural and nonnatural bases including 2′-deoxyzebularine as a central mispair, was studied. Depending on the base present in the middle of the sequence, it is possible to affect the stability of the bimolecular duplex modulating the duplex - hairpin equilibrium. Magnesium ions were shown to stabilize preferentially the bimolecular duplex form. The results indicate the importance of the modifications and the role of cations in shifting the structural equilibrium.