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A Strategy for Sensitive, Large Scale Quantitative Metabolomics
Published on: May 27, 2014
Síntesis estereodivergente de todos los 15-F(2) isoprostanos
Thomas O Schrader1, Marc L Snapper
1Department of Chemistry, Eugene F. Merkert Chemistry Center, Boston College, 2609 Beacon Street, Chestnut Hill, Massachusetts 02467, USA.
Journal of the American Chemical Society
|September 13, 2002
Resumen
Los investigadores sintetizaron todos los isoprostanos 15-F2 conocidos y potenciales, metabolitos lipídicos cruciales relacionados con el estrés oxidativo. Esta biblioteca completa permite la primera comparación directa de estos compuestos en estudios biológicos.
Área de la Ciencia:
- Los lipidómicos también.
- Química orgánica es la química orgánica.
- La bioquímica es la bioquímica.
Sus antecedentes:
- Los isoprostanos son metabolitos lipídicos formados por la oxidación de los radicales libres del ácido araquidónico.
- Se detectan en condiciones de estrés oxidativo, pero sus funciones biológicas y objetivos siguen siendo en gran medida desconocidos.
- Comprender la función del isoprostano es fundamental para elucidar las vías del estrés oxidativo.
Objetivo del estudio:
- Para sintetizar una biblioteca completa de todos los isoprostanos 15-F2 conocidos y anticipados.
- Proporcionar a los investigadores herramientas esenciales para investigar el significado biológico de los isoprostanos.
- Para permitir la primera evaluación directa, lado a lado, de los estereoisómeros individuales del isoprostano.
Principales métodos:
- Se empleó una estrategia sintética estereodivergente, con metátesis de apertura de anillos para instalar cadenas laterales cis-alquilo características.
- Los estereoisómeros individuales se resolvieron utilizando una reducción asimétrica catalítica o un protocolo de separación basado en auxiliares.
- La conversión a los isoprostanos 15-F2 finales implicó una funcionalización directa de la cadena lateral del ácido carboxílico.
Principales resultados:
- La preparación exitosa de una biblioteca completa que abarca todos los isoprostanos 15-F2 conocidos y anticipados.
- La metodología permite el aislamiento de estereoisómeros individuales.
- La biblioteca sintetizada proporciona una plataforma para ensayos biológicos comparativos.
Conclusiones:
- La síntesis completa de la biblioteca de isoprostano 15-F2 es un avance significativo en la investigación del estrés oxidativo.
- Este recurso facilita la investigación detallada de las actividades biológicas del isoprostano y los objetivos celulares.
- Los estudios futuros ahora pueden comparar directamente los efectos de diferentes isómeros de isoprostano.
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