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Síntesis de isómeros de azúcares raros mediante epimerización selectiva del sitio

Yong Wang¹, Hayden M Carder¹, Alison E Wendlandt²

¹Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, USA.

|January 16, 2020

Resumen

Los investigadores desarrollaron un nuevo método para crear azúcares raros directamente a partir de carbohidratos de biomasa utilizando epimerización selectiva del sitio. Este avance ofrece una ruta más accesible a estos valiosos compuestos, importantes en los productos farmacéuticos.

Área de la Ciencia:

Química de los carbohidratos
Síntesis orgánica
Valorización de la biomasa

Sus antecedentes:

Los glicanos juegan un papel crucial en numerosos procesos fisiológicos.
Mientras que los azúcares comunes son abundantes, los monosacáridos raros son difíciles de aislar y requieren una síntesis compleja.
Los azúcares raros son componentes vitales en muchos productos farmacéuticos, incluidos los antivirales y los anticancerígenos.

Objetivo del estudio:

Desarrollar un método sintético directo para la producción de isómeros de azúcares raros a partir de carbohidratos derivados de la biomasa.
Establecer una estrategia concisa y eficiente para el acceso a valiosos compuestos de azúcares raros.

Principales métodos:

Reacciones de epimerización selectiva del sitio en los carbohidratos de la biomasa.
Estudios mecanicistas relacionados con la abstracción y donación secuencial de átomos de hidrógeno.
La catálisis está mediada por dos sistemas catalíticos distintos.

Principales resultados:

Preparación exitosa de isómeros de azúcares raros directamente de carbohidratos de biomasa fácilmente disponibles.
Demostración de un mecanismo de reacción controlado cinéticamente.
Identificación de las principales etapas catalíticas que implican la transferencia de átomos de hidrógeno.

Conclusiones:

La estrategia sintética desarrollada proporciona un enfoque simplificado para la síntesis de azúcares raros.
Este método ofrece un acceso potencialmente amplio a una clase valiosa de productos naturales.
Los hallazgos allanan el camino para una utilización más eficiente de la biomasa para los precursores farmacéuticos.

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