Artículo
Escherichia coli β-Galactosidase Inhibitors through Modifications at the Aglyconic Moiety: Experimental Evidence of Conformational Distortion in the Molecular Recognition Process
Calle, Luis; Roldós, Virginia; Cañada, Javier F.; Uhrig, Maria Laura
; Cagnoni, Alejandro
; Manzano, Veronica Elena
; Varela, Oscar Jose
; Jiménez Barbero, Jesús
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Fecha de publicación:
03/2013
Editorial:
Wiley
Revista:
Chemistry- A European Journal
ISSN:
0947-6539
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
Herein, we describe the use of thioglycosides as glycosidase inhibitors by employing novel modifications at the reducing end of these glycomimetics. The inhibitors display a basic galactopyranosyl unit (1-4)-bonded to a 3-deoxy-4-thiopentopyranose moiety. The molecular basis of the observed inhibition has been studied by using a combination of NMR spectroscopy and molecular modeling techniques. It is demonstrated that these molecules are not recognized by Escherichia coli bgalactosidase in their ground-state conformation, with a conformational selection process taking place. In fact, the observed conformational distortion depends on the chemical nature of the compounds and results from the rotation around the glycosidic linkage (variation of F or Y) or from the deformation of the six-membered ring of the pentopyranose. The bound conformations of the ligand are adapted in the enzymatic pocket with a variety of hydrogen-bond, van der Waals, and stacking interactions.
Palabras clave:
Conformation Analysis
,
Enzyme Models
,
Glycosides
,
Nmr Spectroscopy
,
S Ligands
Archivos asociados
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Identificadores
Colecciones
Articulos(CIHIDECAR)
Articulos de CENTRO DE INVESTIGACIONES EN HIDRATOS DE CARBONO
Articulos de CENTRO DE INVESTIGACIONES EN HIDRATOS DE CARBONO
Articulos(INQUIMAE)
Articulos de INST.D/QUIM FIS D/L MATERIALES MEDIOAMB Y ENERGIA
Articulos de INST.D/QUIM FIS D/L MATERIALES MEDIOAMB Y ENERGIA
Citación
Calle, Luis; Roldós, Virginia; Cañada, Javier F.; Uhrig, Maria Laura; Cagnoni, Alejandro; et al.; Escherichia coli β-Galactosidase Inhibitors through Modifications at the Aglyconic Moiety: Experimental Evidence of Conformational Distortion in the Molecular Recognition Process; Wiley; Chemistry- A European Journal; 19; 13; 3-2013; 4262-4270
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