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Los rotameres de enlaces de amida cis-trans en β-peptoides y peptoides: evaluación de los efectos estereoelectrónicos
Jonas S Laursen1, Jens Engel-Andreasen, Peter Fristrup
1Department of Chemistry, Technical University of Denmark, Kemitorvet 207, DK-2800, Kongens Lyngby, Denmark.
Journal of the American Chemical Society
|January 25, 2013
Resumen
Los investigadores exploraron las variaciones estructurales en los β-peptoides, encontrando que los grupos tioamida y trifluoroacetil mejoran la preferencia por la cis-amida. Esto ofrece nuevas estrategias para controlar el plegamiento de peptoides y estabilizar conformaciones a través de nuevos enlaces de hidrógeno.
Área de la Ciencia:
- * Química supramolecular y ciencias de los materiales.
- * Química medicinal y diseño de fármacos.
Sus antecedentes:
- * Los análogos de péptidos no naturales, incluidos los β-peptoides (N-alquilo-β-alaninas), son prometedores para nuevos materiales y ligandos farmacológicamente activos.
- * La propensión al plegamiento de los β-peptoides sigue siendo poco explorada, particularmente con respecto a los equilibrios de enlaces amídicos cis-trans.
Objetivo del estudio:
- * Para investigar el impacto de las modificaciones estructurales en los equilibrios de los enlaces amídicos cis-trans en los sistemas de monómero β-peptoide.
- * Para sintetizar y analizar nuevos análogos de peptoides y β-peptoides que contienen grupos tioamida y trifluoroacetil.
- * Explorar la influencia de estas modificaciones en la propensión al plegamiento de los peptoides y la estabilidad conformacional.
Principales métodos:
- * Síntesis de nuevos análogos de peptoides y β-peptoides, incluidas las variantes de tioamida y trifluoroacetil.
- * Espectroscopia de Resonancia Magnética Nuclear (RMN) para el estudio del isomerismo cis-trans.
- * Análisis cristalográfico de rayos X para determinar las estructuras moleculares.
- * Cálculos de la Teoría Funcional de Densidad (DFT) para modelar interacciones y conformaciones.
Principales resultados:
- * Las variaciones estructurales, incluidas las modificaciones de la cadena lateral, influyen en los equilibrios de enlaces amídicos cis-trans, consistentes con los estudios de α-peptoides.
- * Se sintetizaron e investigaron los primeros ejemplos de peptoides y β-peptoides con grupos tioamida y trifluoroacetil.
- * Estos nuevos análogos mostraron una mayor preferencia por las cisamidas en comparación con los compuestos madre.
- * Se observó evidencia para la estabilización de las interacciones tioamida-aromáticas a través de la unión de hidrógeno C ((sp ((2)) -H · · · S ((amida).
Conclusiones:
- * La introducción de grupos tioamida y trifluoroacetil en las estructuras peptoide y β-peptoide aumenta la preferencia por las cis-amidas.
- * Estos hallazgos proporcionan nuevas estrategias para modular el plegamiento de construcciones basadas en peptoides.
- * Las interacciones tioamida-aromáticas representan un factor significativo en la estabilización de las conformaciones específicas de los peptoides.
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