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Efectos de la sustitución de un grupo OH por un átomo F en D-glucosa. Análisis Ab initio y DFT
1Contribution from the Quantum Chemistry Group, Faculty of Chemistry, A. Mickiewicz University, ul. Grunwaldzka 6, 60-780 Poznan, Poland.
Journal of the American Chemical Society
|July 18, 2001
Resumen
La sustitución del flúor en la D-glucosa crea 4-deoxy-4-fluoro-D-glucosa, un potencial candidato a fármaco. Este azúcar modificado mantiene estructuras similares y actividad biológica a la D-glucosa, especialmente en compuestos cíclicos con libertad de conformación limitada.
Área de la Ciencia:
- Química computacional es la química computacional.
- Química de los carbohidratos Química de los carbohidratos
- Química Medicinal La Química Medicinal es el campo de la Química Medicinal.
Sus antecedentes:
- La D-glucosa es un monosacárido fundamental con importantes funciones biológicas.
- Comprender las propiedades estructurales y energéticas de los análogos de glucosa es crucial para el diseño de fármacos.
- La sustitución de flúor es una estrategia común en la química medicinal para modular las propiedades de los fármacos.
Objetivo del estudio:
- Investigar computacionalmente las diferencias estructurales y energéticas entre la D-glucosa y la 4-deoxy-4-fluoro-D-glucosa.
- Evaluar el impacto de la sustitución de flúor en las redes intramoleculares de enlaces de hidrógeno.
- Para evaluar el potencial de la 4-deoxy-4-fluoro-D-glucosa como un fármaco de plomo.
Principales métodos:
- Se emplearon métodos de alto nivel ab initio y de Teoría Funcional de Densidad (DFT).
- Los cálculos incluyeron los niveles de teoría MP2 y B3LYP con varios conjuntos de base.
- Se utilizó el modelo de disolución 5.4/AM1 para simular los efectos de la solución acuosa.
Principales resultados:
- La sustitución de flúor en 4-deoxy-4-fluoro-D-glucosa desestabilizó los enlaces de hidrógeno intramoleculares en la fase gaseosa.
- Las anomalías alfa mostraron una mayor estabilización en la 4-deoxy-4-fluoro-D-glucosa en comparación con la D-glucosa.
- Tanto la D-glucosa como su análogo 4-deoxy-4-fluoro existen como una mezcla de tres conformadores principales en solución acuosa.
Conclusiones:
- La 4-deoxy-4-fluoro-D-glucosa exhibe preferencias conformacionales similares a la D-glucosa, lo que sugiere una actividad bioquímica comparable.
- La sustitución de flúor en moléculas cíclicas conformacionalmente restringidas puede conducir a un diseño de fármacos exitoso.
- Este estudio pone de relieve el potencial de la 4-deoxy-4-fluoro-D-glucosa como un fármaco candidato viable.
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