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Solid-phase Submonomer Synthesis of Peptoid Polymers and their Self-Assembly into Highly-Ordered Nanosheets
Published on: November 2, 2011
Ajuste de la estructura secundaria peptoide con funcionalidad pentafluoroaromática: un nuevo paradigma de diseño para
Benjamin C Gorske1, Helen E Blackwell
1Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1322, USA.
Journal of the American Chemical Society
|November 2, 2006
Resumen
Los investigadores exploraron cómo los grupos pentafluoroaromáticos afectan las estructuras peptoides. La introducción de un monómero fluorado específico (S) -N-{1-{pentafluorofenil) etil) glicina puede controlar si los peptoides forman bucles o hélices.
Área de la Ciencia:
- Química de Polímeros La Química de Polímeros es la química de los polímeros.
- Química supramolecular de las moléculas.
- Síntesis orgánica La síntesis orgánica.
Sus antecedentes:
- Los peptoides (oligómeros de glicina sustituidos por N) imitan los péptidos naturales y son valiosos para estudiar las interacciones biomoleculares y desarrollar biomimética.
- La conformación de los peptoides, particularmente aquellos con cadenas laterales quirales aromáticas, está influenciada por factores como el disolvente y la longitud de la cadena, lo que lleva a estructuras de bucle helicoidal o roscado.
- Comprender el control conformacional es clave para diseñar peptoides con estructuras específicas y novedosas.
Objetivo del estudio:
- Investigar el impacto de la funcionalidad pentafluoroaromática en los perfiles conformacionales de los peptoides.
- Para sintetizar y caracterizar nuevos peptoides que incorporan un bloque de construcción fluorado, (S) -1- (pentafluorofenil) etilamina.
- Explorar el papel del pi-stacking y la electrostática en el plegamiento de peptoides y las preferencias conformacionales.
Principales métodos:
- Síntesis de un nuevo bloque de construcción de aminas alfa-quirales, (S) -1- (pentafluorofenil) etilamina (S-2).
- Preparación de homo- y heteropeptoides utilizando S-2 y sus análogos no fluorados.
- Caracterización de peptoides sintetizados utilizando dicroísmo circular (CD) y espectroscopia de resonancia magnética nuclear (RMN).
Principales resultados:
- El grupo pentafluorofenilo no mejoró significativamente las interacciones de apilamiento de pi en los heteropeptoides.
- La incorporación de monómeros de (S) -N- (((1- ((pentafluorofenil) etil) glicina indujo estructuras helicoidales en peptoides que típicamente forman bucles.
- Un solo monómero de (S) -N- ((1- ((pentafluorofenil) etil) glicina podría controlar selectivamente las conformaciones en bucle o helicoidales ajustando las propiedades electrónicas.
Conclusiones:
- La funcionalidad pentafluoroaromática ofrece una nueva estrategia para manipular la estructura peptoidea.
- La colocación estratégica del monómero (S) -N- ((1- ((pentafluorofenil) etil) glicina proporciona un control preciso sobre la arquitectura de los peptoides.
- Este enfoque permite la construcción de nuevas estructuras peptoides con propiedades conformacionales a medida.
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