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Hidrocarburos lineales y helicoidales con cadenas laterales extendidas
Lin Guo1, Oliver J Dutton1, Murat Kucukdisli1
1School of Chemistry, University of Bristol, BS8 1TS, Bristol, U.K.
Journal of the American Chemical Society
|September 30, 2021
Resumen
Las cadenas flexibles de hidrocarburos con conformaciones controladas son cruciales para la medicina y los materiales. Los nuevos patrones de sustitución permiten grandes grupos en cadenas lineales o helicoidales, lo que permite un diseño molecular preciso para aplicaciones como la segmentación de fármacos.
Área de la Ciencia:
- Química orgánica
- Química supramolecular
- Ciencias de los materiales
Sus antecedentes:
- Las moléculas flexibles controladas conformalmente son vitales para aplicaciones donde la forma molecular y la adaptabilidad son clave.
- La conformación de la cadena de hidrocarburos generalmente se rige evitando las interacciones sin-pentano, lo que lleva a estructuras lineales (sin-anti) o helicoidales (todas sin).
- La incorporación de grandes sustituyentes a menudo conduce a interacciones sinpentano inevitables, lo que dificulta el control conformacional.
Objetivo del estudio:
- Identificar patrones de sustitución que permitan la incorporación de grandes grupos en cadenas de hidrocarburos controladas conformacionalmente.
- Diseñar moléculas flexibles con conformaciones lineales o helicoidales predecibles para aplicaciones específicas.
- Para superar las limitaciones en el control de la conformación impuestas por sustitutos voluminosos en cadenas flexibles.
Principales métodos:
- Análisis computacional para predecir el comportamiento conformacional.
- Síntesis química de nuevos derivados de hidrocarburos.
- Espectroscopia de resonancia magnética nuclear (RMN) para el análisis estructural y conformacional.
Principales resultados:
- Se consiguen conformaciones casi lineales (95%) en hidrocarburos sinanti con cadenas laterales de acetoxietil mediante la adopción de conformaciones eclipsadas no ideales.
- Demostrado que el mantenimiento de conformaciones helicoidales en hidrocarburos all-syn requiere la eliminación estratégica de grupos metilo adyacentes.
- Incorporó con éxito grandes sustituyentes en esqueletos de hidrocarburos lineales y helicoidales mientras conservaba la integridad conformacional.
Conclusiones:
- Estrategias desarrolladas para diseñar cadenas flexibles de hidrocarburos controladas conformacionalmente con grandes sustituyentes.
- Permitió la orientación precisa de grupos funcionales para aplicaciones en unión multivalente y reactividad cooperativa.
- Abrió el camino para diseñar moléculas dirigidas a las interacciones proteína-proteína en contextos relevantes para la enfermedad.
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