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La señalización por resonancia magnética nuclear de la información quiral molecular utilizando un reactivo aquiral
Atsuomi Shundo1, Jan Labuta, Jonathan P Hill
1World Premier International Research Center for Materials Nanoarchitectonics (MANA), National Institute for Materials Science, 1-1 Namiki, Tsukuba 305-0044, Japan.
Journal of the American Chemical Society
|June 24, 2009
Resumen
Un anfitrión oxoporfirinógeno achiral permite la detección por resonancia magnética nuclear (RMN) de la quiralidad del huésped. Este método determina el exceso enantiomérico (ee) mediante la observación de la división de la señal de RMN del huésped, un nuevo enfoque para el análisis quiral.
Área de la Ciencia:
- Química supramolecular de las moléculas.
- Química Analítica La Química Analítica es la
- Química orgánica es la química orgánica.
Sus antecedentes:
- La discriminación quiral generalmente requiere anfitriones quirales o auxiliares para la detección de RMN.
- Los métodos existentes se basan en la formación de complejos diastereoméricos, lo que limita las aplicaciones del huésped achiral.
Objetivo del estudio:
- Para demostrar un huésped achiral para la señalización de la quiralidad del huésped utilizando espectroscopia de RMN.
- Establecer un nuevo método para determinar el exceso enantiomérico (ee) de ácidos alfa-hidroxicarboxílicos.
Principales métodos:
- Utilizó un oxoporfirinógeno achiral como molécula huésped.
- Se empleó la espectroscopia de RMN de 1H para observar la división de resonancia del huésped.
- Se realizaron análisis espectroscópicos UV/vis, CD y FT-IR.
Principales resultados:
- El oxoporfirinógeno achiral señaló con éxito la información quiral de los ácidos alfa-hidroxicarboxílicos.
- El exceso enantiomérico (ee) se determinó mediante la división de las señales de RMN de 1H del huésped achiral.
- Se propuso una estequiometría compleja anfitrión-invitado 1:2 y una tautomerización impulsada por protonación.
Conclusiones:
- Los anfitriones achirales pueden detectar la quiralidad del huésped, expandiendo el análisis quiral basado en RMN.
- La división de la señal de RMN del anfitrión ofrece un nuevo paradigma para la determinación de EE.
- Los hallazgos abren caminos para el desarrollo de nuevas tecnologías de detección quiral.
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