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Biochemical Titration of Glycogen In vitro
Published on: November 25, 2013
C2-amidoglucosilación. también conocido como C2-amidoglucosilación. Alcance y mecanismo de la transferencia de
1Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
Journal of the American Chemical Society
|August 15, 2002
Resumen
Este estudio introduce una nueva reacción de una sola olla para sintetizar 2-N-acil-2-deoxy-beta-pyranosides. El método crea de manera eficiente glucoconjugados complejos con la introducción de nitrógeno estereoselectivo y la formación de enlaces glucosídicos.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química de los carbohidratos Química de los carbohidratos
- Química sintética de la química sintética.
Sus antecedentes:
- Las reacciones de glicosilación son fundamentales en la química de los carbohidratos.
- El desarrollo de métodos eficientes para sintetizar carbohidratos modificados es crucial para el descubrimiento de fármacos y la glucobiología.
- La introducción de funcionalidades en la posición C2 de los piranosidos a menudo requiere procedimientos de varios pasos.
Objetivo del estudio:
- Desarrollar una nueva reacción de C2-amidoglicosilación de un solo recipiente.
- Para sintetizar 2-N-acil-2-deoxy-beta-piranósidos a partir de glicálicos fácilmente disponibles. para la síntesis de 2-N-acil-2-deoxy-beta-piranósidos a partir de glicálicos fácilmente disponibles. para la síntesis de 2-N-acil-2-deoxy-beta-piranósidos a partir de glicálicos fácilmente disponibles. para la síntesis de 2-N-acil-2-deoxy-beta-piranósidos a partir de glicálicos fácilmente disponibles.
- Para lograr la introducción estereoselectiva de funcionalidades de amida en la posición C2.
Principales métodos:
- La activación de los donantes glicosídicos mediante el uso de tiantreno-5-óxido y Tf2O.
- Reacción posterior con nucleófilos de amida y aceptores de glicosilo.
- Espectroscopia de RMN a baja temperatura con etiquetado de isótopos (15N, 18O) para estudios mecanicistas.
Principales resultados:
- Síntesis exitosa de varios conjugados C2-amidoglicónicos en un procedimiento de una sola olla.
- Demostración de la transferencia estereoselectiva de C2-nitrógeno y la formación de enlaces glucosídicos.
- Identificación de los principales intermediarios, incluido un C2-sulfonio glicosil imidato y una oxazolina.
Conclusiones:
- La reacción de un solo recipiente descrita ofrece una ruta eficiente a los conjugados C2-amidoglicónicos.
- La metodología permite la incorporación de diversas funcionalidades de amida.
- El estudio proporciona conocimientos mecanicistas sobre este nuevo proceso de glicosilación oxidativa.
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