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Elucidación estereoquímica y síntesis total de dihidropacidamicina D, una pacidamicina semisintética

C G Boojamra¹, R C Lemoine, J C Lee

¹Microcide Pharmaceuticals, Inc., 850 Maude Avenue, Mountain View, California 94043, USA.

Journal of the American Chemical Society

|July 18, 2001

Resumen

Las dihidropacidamicinas semisintéticas conservan su actividad antimicrobiana. Se logró un análisis estereoquímico detallado de la pacidamicina D y sus derivados a través de la degradación y la síntesis total.

Área de la Ciencia:

Química de Productos Naturales Química de Productos Naturales
Química Medicinal La Química Medicinal es el campo de la Química Medicinal.
Síntesis orgánica La síntesis orgánica.

Sus antecedentes:

Las pacidamicinas son productos naturales con propiedades antimicrobianas.
Las modificaciones semisintéticas pueden producir compuestos con actividad similar o mejorada.
La estereoquímica es crucial para la actividad biológica.

Objetivo del estudio:

Para sintetizar dihidropacidamicinas a través de la hidrogenación de las pacidamicinas.
Para aclarar la estereoquímica completa de la pacidamicina D.
Para confirmar la configuración estereoquímica de los residuos de aminoácidos y el sitio de nucleósidos.

Principales métodos:

Hidrogenación de la olefina exocíclica C ((4') de las pacidamicinas.
Experimentos de degradación de los productos naturales.
Síntesis total de la dihidropacidamicina D.

Principales resultados:

Las dihidropacidamicinas semisintéticas exhibieron una actividad antimicrobiana comparable a las pacidamicinas naturales.
Las identidades estereoquímicas de los residuos de triptófano y alanina en la pacidamicina D se confirmaron como (S).
Se determinó que el residuo de ácido 3-metilamino-2-aminobutírico era (2S,3S), y el sitio nucleósido C(4') era (R) después de la hidrogenación.

Conclusiones:

La hidrogenación de las pacidamicinas produce análogos semisintéticos activos.
La estereoquímica de la pacidamicina D y sus componentes ha sido completamente aclarada.
Las configuraciones estereoquímicas establecidas proporcionan una base para comprender las relaciones estructura-actividad.

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