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Síntesis total de la clorofusina, sus siete diastereómeros cromóforos y estructuras parciales clave
Ryan C Clark1, Sang Yeul Lee, Dale L Boger
1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Journal of the American Chemical Society
|August 21, 2008
Resumen
Se logró la síntesis total de clorofusina, un inhibidor natural de la formación del complejo p53-MDM2. Este estudio asignó la estereoquímica absoluta y reasignó la estereoquímica relativa de su complejo cromóforo.
Área de la Ciencia:
- Síntesis de Productos Naturales.
- Química Medicinal La Química Medicinal es un campo de estudio de la química medicinal.
- Química orgánica es la química orgánica.
Sus antecedentes:
- La clorofusin es un inhibidor natural de la formación del complejo p53-MDM2.
- Su estructura presenta un cromóforo azaphilone vinculado a un péptido cíclico a través de la ornitina.
Objetivo del estudio:
- Para reportar la síntesis total de clorofusina.
- Para asignar la estereoquímica absoluta del cromóforo de la clorofusina.
- Para reasignar la estereoquímica relativa del cromóforo de la clorofusina.
Principales métodos:
- Síntesis de los precursores de los cromóforos de la azaphilona y los dipeptidos ornitina-treonina.
- Reacciones de condensación y oxidación/espirociclado en un solo paso para generar diastereómeros.
- Análisis espectroscópico (NMR, MS) para la asignación estereoquímica.
- Enfoque de síntesis total convergente. enfoque de síntesis total convergente.
Principales resultados:
- Sintetizó con éxito los ocho diastereómeros del conjugado cromóforo-dipeptido.
- Se le ha asignado la (4R,8S,9R) estereoquímica del cromóforo natural de la clorofusina.
- Confirmó la reasignación estereoquímica y estableció la estereoquímica absoluta de la clorofusina.
- Sintetizó los siete diastereómeros cromóforos posibles restantes de clorofusin.
Conclusiones:
- Se completó con éxito la síntesis total de clorofusina.
- La estereoquímica absoluta y relativa del cromóforo de la clorofusina fue asignada definitivamente.
- Este trabajo proporciona acceso a varios diastereómeros de clorofusina para una mayor evaluación biológica.
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