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Síntesis química en fase sólida de fosfonoacetato y tiofosfonoacetato de oligodeoxinucleótidos

Douglas J Dellinger¹, David M Sheehan, Nanna K Christensen

¹Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO 80309-0215, USA.

Journal of the American Chemical Society

|January 23, 2003

Resumen

Los nuevos oligodeoxinucleótidos de fosfonoacetato y tiofosfonoacetato fueron sintetizados utilizando métodos de fase sólida. Estos análogos de ADN modificado son estables y estimulan la actividad de la RNasa H1.

Área de la Ciencia:

Química del oligonucleótido Química del oligonucleótido
Química medicinal Química medicinal es el campo de la química medicinal.

Sus antecedentes:

Los oligodeoxinucleótidos son cruciales en la biología molecular y la terapéutica.
El desarrollo de oligonucleótidos modificados mejora la estabilidad y la actividad biológica.

Objetivo del estudio:

Para sintetizar nuevos oligodeoxinucleótidos de fosfonoacetato y tiofosfonoacetato.
Para evaluar la estabilidad y la actividad enzimática de estos análogos de ADN modificado.

Principales métodos:

Síntesis en fase sólida utilizando nuevos monómeros de fosfinodiamidita.
Síntesis automatizada de ADN con modificación de ácido fosfonoacético.
Oxidación cuantitativa y purificación a través de HPLC.
Caracterización mediante RMN y espectrometría de masas.

Principales resultados:

Se han sintetizado con éxito oligodeoxinucleótidos de fosfonoacetato y tiofosfonoacetato con >97% de eficiencia de acoplamiento.
Los oligonucleótidos modificados demostraron estabilidad contra la fosfodiesterasa del veneno de serpiente.
Los análogos mostraron estimulación de la actividad de la RNasa H1.

Conclusiones:

La estrategia de fase sólida desarrollada permite una síntesis eficiente de los oligonucleótidos modificados por el fosfonoacetato y el tiofosfonoacetato.
Estos nuevos análogos poseen propiedades bioquímicas favorables, incluida la resistencia a la nucleasa y la interacción RNase H1.

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