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Homooligómeros cíclicos de aminoácidos azucarados: síntesis, análisis conformacional y significado

E Locardi¹, M Stöckle, S Gruner

¹Institut für Organische Chemie und Biochemie, Technische Universität München, Lichtenbergstrasse 4, D-85747 Garching, Germany.

Journal of the American Chemical Society

|August 23, 2001

Resumen

Se sintetizaron nuevos aminoácidos azucarados (AAS) en oligómeros cíclicos. Estos nuevos SAA cíclicos muestran potencial como moléculas huésped, formando complejos de inclusión con moléculas invitadas como el ácido benzoico.

Área de la Ciencia:

Química de los carbohidratos Química de los carbohidratos
Química supramolecular de las moléculas.
Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

Los aminoácidos azucarados (AAS) son nuevos bloques de construcción con grupos amino y carboxilo en un andamio de carbohidratos.
La síntesis anterior de oligómeros cíclicos involucró principalmente unidades no SAA.

Objetivo del estudio:

Para sintetizar homooligómeros lineales y cíclicos de aminoácidos azucarados.
Investigar las propiedades conformacionales y las capacidades de complejación huésped-huésped de estos nuevos SAA cíclicos.

Principales métodos:

Procedimientos de acoplamiento de la fase sólida y de la fase en solución para la oligomerización y la ciclización.
Síntesis de homooligómeros que contienen dos, tres, cuatro y seis unidades de metilamina (Guma) de ácido glucosiluronico.
Espectroscopia de RMN (cambios químicos, relajaciones T, coeficientes de difusión) para estudiar la complicación huésped-huésped.

Principales resultados:

Se lograron altos rendimientos y cortos tiempos de acoplamiento para la oligomerización y ciclización de la goma.
Se logró por primera vez la síntesis de oligómeros cíclicos compuestos únicamente por AAS.
La complejación del ácido benzoico y el p-nitrofenol por el hexámero cíclico se confirmó a través de estudios espectroscópicos y de difusión.

Conclusiones:

Se sintetizaron con éxito nuevos oligómeros de aminoácidos de azúcares cíclicos.
Estos AAS cíclicos exhiben un comportamiento de complejación huésped-huésped similar a la ciclodextrina.
Los hallazgos abren caminos para el desarrollo de nuevas estructuras supramoleculares basadas en andamios de carbohidratos.

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