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Ligamientos rápidos con reactivos equimolares en agua con la formación de amida del aciltrifluoroborato de potasio

Hidetoshi Noda¹, Gábor Erős, Jeffrey W Bode

¹Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich, 8093 Zürich, Switzerland.

Journal of the American Chemical Society

|April 2, 2014

Resumen

Las ligaduras formadoras de amidas quimioselectivas que utilizan aciltrifluoroboratos de potasio (KAT) y O-carbamoilhidroxilaminas permiten una bioconjugación rápida. Este método une eficientemente diversas moléculas, incluidas las cadenas PEG y la biotina, a los péptidos sin proteger grupos.

Área de la Ciencia:

Química orgánica es la química orgánica.
Bioconjugación Química de la bioconjugación

Sus antecedentes:

El desarrollo rápido de reacciones quimioselectivas es crucial para la síntesis moderna.
Los métodos existentes a menudo requieren la protección de grupos, lo que complica los procedimientos.

Objetivo del estudio:

Introducir una nueva reacción de ligado formador de amidas altamente quimioselectiva.
Para demostrar la utilidad de esta reacción para la bioconjugación en condiciones suaves.

Principales métodos:

Se utilizan aciltrifluoroboratos de potasio (KAT) y O-carbamoilhidroxilaminas para la formación de enlaces amídicos.
Se realizan ligaduras en un péptido de 31 meros sin protección (análogo de GLP-1) con varios grupos funcionales.

Principales resultados:

Se logró una constante de velocidad de segundo orden de 20 M−1s−1 para la ligadura.
Conjugó con éxito cadenas de PEG (hasta 20.000 Mw), lípidos, biotina y tintes al péptido.
Se ha demostrado una eficiente conjugación a bajas concentraciones (1 mM y 100 μM) en minutos u horas.

Conclusiones:

Esta ligadura basada en KAT ofrece una nueva y poderosa herramienta para sintetizar moléculas complejas.
La alta quimioselectividad y eficiencia de la reacción facilitan la creación de conjugados proteína-proteína y proteína-polímero.

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