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Los derivados de la O6-(benzotriazol-1-il)inosina: son nucleósidos reactivos y de fácil síntesis
Suyeal Bae1, Mahesh K Lakshman
1Department of Chemistry, The City College and The City University of New York, 138th Street at Convent Avenue, New York, New York 10031-9198, USA.
Journal of the American Chemical Society
|January 25, 2007
Resumen
Un nuevo método sintetiza los derivados de la O6-(benzotriazol-1-il)inosina a partir de la inosina y el reactivo BOP. Estos derivados nucleósidos estables son efectivos para las reacciones de SNAr y la modificación del ADN.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química de nucleósidos Química de nucleósidos
- Química Medicinal La Química Medicinal es el campo de la Química Medicinal.
Sus antecedentes:
- La inosina y la 2'-deoxyinosina son nucleósidos fundamentales.
- El desarrollo de nuevos derivados de nucleósidos es crucial para la biología química y el descubrimiento de fármacos.
- Las rutas sintéticas eficientes para los nucleósidos modificados son muy buscadas.
Objetivo del estudio:
- Desarrollar un método nuevo y conveniente para la síntesis de O6-(benzotriazol-1-il)inosina y sus derivados 2'-desoxi.
- Para explorar la reactividad de estos nuevos derivados de nucleósidos.
- Para preparar y evaluar un bloque de construcción de ADN para la modificación de ADN específico del sitio.
Principales métodos:
- Reacción de la inosina o de la 2'-deoxinosina con el 1H-benzotriazol-1-iloxi-tris (dimetilamino) fosfonio hexafluorofosfato (BOP).
- Aislamiento y caracterización de productos intermedios y productos utilizando técnicas como la RMN 31P{1H}.
- Síntesis de varios derivados nucleosídicos, incluyendo dímeros y conjugados.
- Preparación de un bloque de construcción de fosforamidita para la síntesis de ADN.
Principales resultados:
- Se sintetizó con éxito una nueva clase de derivados de la O6-(benzotriazol-1-il)inosina y la 2'-deoxyinosina.
- Estos derivados actúan como nucleósidos electrófilos efectivos, reaccionando fácilmente con diversos nucleófilos.
- Se lograron estructuras complejas como dímeros con puentes de arilo y conjugados de nucleósidos y aminoácidos.
- Se preparó un derivado de fosforamidita y mostró potencial para la modificación del ADN específico del sitio.
Conclusiones:
- Un método único y simple produce derivados estables y reactivos de ribo y 2'-deoxyribonucleoside.
- Estos derivados de la O6-(benzotriazol-1-il)inosina son sintones versátiles para la química de los SNAr.
- El nucleósido benzotriazolyl nucleoside phosphoramidite es un reactivo prometedor para la modificación del ADN.
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