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Detección biomimética de la quiralidad con piridoxal-5'-fosfato

Samantha L Pilicer¹, Pegah R Bakhshi¹, Keith W Bentley¹

¹Department of Chemistry, Georgetown University , Washington, D.C. 20057, United States.

Journal of the American Chemical Society

|January 28, 2017

Resumen

Este estudio introduce un nuevo ensayo biomimético que utiliza piridoxal-5'-fosfato (PLP) para el análisis de aminoácidos, alcoholes y aminas. El método determina simultáneamente la configuración absoluta, la composición enantiomérica y la concentración con alta sensibilidad.

Área de la Ciencia:

Química analítica
Química biomimética
Análisis quiral

Sus antecedentes:

La determinación precisa de la composición enantiomérica y la configuración absoluta es crucial en varios campos científicos.
Los métodos existentes para analizar compuestos quirales pueden ser complejos y consumir mucho tiempo.

Objetivo del estudio:

Desarrollar un ensayo novedoso, rápido y simultáneo para determinar la configuración absoluta, la composición enantiomérica y la concentración de aminoácidos, aminoalcoholes y aminas sin protección.
Utilizar un ensayo biomimético de desplazamiento del indicador para mejorar la detección quiral.

Principales métodos:

Un ensayo biomimético de desplazamiento del indicador en el que se utiliza el piridoxal-5-ominofosfato (PLP) como reactivo clave.
Metátesis rápida de imina entre una sonda de aril imina de PLP y los analíticos objetivo.
Dicroísmo circular (CD) y espectroscopia de fluorescencia para la detección y el análisis.
Respuesta de fluorescencia desconectada para la determinación de la concentración

Principales resultados:

El ensayo captura con éxito los compuestos objetivo a través de la metástasis de imina, lo que permite el análisis de CD para la determinación del exceso enantiomérico (ee).
Los efectos característicos del algodón observados en la unión del sustrato proporcionan información sobre la configuración absoluta.
Una respuesta de fluorescencia no enantioselectiva e independiente de la composición permite una medición precisa de la concentración total del analito.
El método permite la determinación simultánea de la configuración absoluta, la composición enantiomérica y la concentración.

Conclusiones:

El ensayo biomimético basado en PLP desarrollado ofrece una herramienta poderosa para el análisis quiral simultáneo de aminoácidos, aminoalcoholes y aminas.
Este ensayo proporciona un método sensible y eficiente para determinar la configuración absoluta, la composición enantiomérica y la concentración.
El enfoque tiene un potencial significativo para aplicaciones en análisis farmacéuticos, bioquímica y control de calidad.

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