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Fosfolil (borano) aminoácidos y péptidos: síntesis estereoselectiva y propiedades fluorescentes con un gran

Mathieu Arribat¹, Emmanuelle Rémond¹, Sébastien Clément²

¹Institut des Biomolécules Max Mousseron, IBMM, UMR 5247, CNRS, Université de Montpellier, ENSCM , Place Eugène Bataillon, 34095 Montpellier cedex 5, France.

Journal of the American Chemical Society

|December 22, 2017

Resumen

Se sintetizaron estereoselectivamente nuevos aminoácidos de fosfolil (borano). Estos nuevos aminoácidos no naturales ofrecen diversas cadenas laterales y exhiben propiedades fluorescentes útiles para los péptidos etiquetados y los estudios de relación estructura-actividad.

Área de la Ciencia:

Química orgánica
Química medicinal
La bioquímica

Sus antecedentes:

Los aminoácidos no naturales son cruciales para expandir la diversidad química de los péptidos.
El desarrollo de nuevos aminoácidos con funcionalidades únicas, como la fluorescencia, es un área activa de investigación.

Objetivo del estudio:

Para sintetizar estereoselectivamente nuevos aminoácidos de fosfoil y boro.
Explorar el potencial de derivación y las propiedades fluorescentes de estos nuevos aminoácidos.
Para demostrar su incorporación en péptidos para aplicaciones potenciales.

Principales métodos:

Síntesis estereoselectiva a través de la reacción del anión fosfilo con ésteres α-amino de yodo.
Complejación in situ con el boro.
Desprotección selectiva y acoplamiento de péptidos (C- o N-).

Principales resultados:

Síntesis exitosa de aminoácidos de fosfolil (borano) con diversas posibilidades de cadena lateral.
Incorporación demostrada en péptidos mediante técnicas estándar de acoplamiento de péptidos.
Propiedades fluorescentes observadas con un gran desplazamiento de Stokes (160 nm) y una emisión de hasta 535 nm.

Conclusiones:

Los aminoácidos fosfolílicos (borano) representan una nueva clase de aminoácidos no naturales.
Estos compuestos son versátiles bloques de construcción para la creación de péptidos funcionales.
Sus propiedades fluorescentes los convierten en candidatos prometedores para el desarrollo de péptidos etiquetados y estudios SAR.

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