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Uso de una deshidrogenasa robusta de un arqueo hipertermófilo en catálisis asimétrica - entrada dinámica de
Jacob A Friest1, Yukari Maezato, Sylvain Broussy
1Department of Chemistry, University of Nebraska, Lincoln, Nebraska 68588, USA.
Journal of the American Chemical Society
|April 10, 2010
Resumen
Este estudio introduce una deshidrogenasa de alcohol eficiente (SsADH-10) de Sulfolobus solfataricus para la síntesis asimétrica. La enzima permite una resolución cinética dinámica reductora dinámica (DYRKR) altamente selectiva de aldehídos de tipo profeno, lo que demuestra una amplia tolerancia al sustrato y reciclabilidad.
Área de la Ciencia:
- Biocatálisis y síntesis asimétrica.
- Ingeniería de enzimas y sus aplicaciones.
- Arqueas hipertermófilas Bioquímica de las arqueas hipertermófilas
Sus antecedentes:
- La síntesis quiral de fármacos antiinflamatorios no esteroideos (AINE) y compuestos relacionados es crucial.
- Los métodos enzimáticos ofrecen rutas sostenibles para la síntesis enantioselectiva.
- Las enzimas hipertermofílicas presentan propiedades únicas para aplicaciones industriales.
Objetivo del estudio:
- Desarrollar un sistema de expresión heterólogo eficiente para el Sulfolobus solfataricus ADH-10 (SsADH-10).
- Para utilizar SsADH-10 para la resolución dinámica reductiva cinética (DYRKR) de sustratos de 2-arilpropanal (tipo de profeno).
- Para investigar la estereoselectividad de la enzima, el alcance del sustrato y la reciclabilidad en síntesis asimétrica.
Principales métodos:
- La expresión heteróloga del Sulfolobus solfataricus ADH-10.
- Síntesis de sustratos de 2-arilpropanal a través de la alfa-arilación de Buchwald-Hartwig y posterior reducción.
- Resolución cinética reductora dinámica enzimática (DYRKR) utilizando el SsADH-10, el NADH catalítico y el amortiguador de fosfato a 80°C.
- Modelado in silico para predecir la tolerancia del sustrato.
Principales resultados:
- SsADH-10 demostró una eficiente expresión y actividad heteróloga en DYRKR.
- Se lograron altas enantioselectividades (EE > 90%) para 9 cadenas laterales de arilo, incluidas las de los principales AINE.
- Se observó una preferencia por el antipodo (S) en los sustratos de tipo profeno probados.
- La enzima exhibió una amplia tolerancia al sustrato y pudo reciclarse a través del ciclo térmico sin pérdida de enantioselectividad.
Conclusiones:
- SsADH-10 es un nuevo biocatalizador para la síntesis asimétrica, particularmente eficaz en DYRKR de aldehídos de tipo profeno.
- Este trabajo representa la primera aplicación de una deshidrogenasa hipertermofílica Sulfolobus en síntesis asimétrica y DYRKR.
- La robustez y reciclabilidad de SsADH-10 resaltan el potencial de las enzimas arqueas en la síntesis quiral sostenible.
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