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Abstract:

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 β-galactosidase 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 φ or σ) 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. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Registro:

Documento: Artículo
Título:Escherichia coli β-galactosidase inhibitors through modifications at the aglyconic moiety: Experimental evidence of conformational distortion in the molecular recognition process
Autor:Calle, L.; Roldós, V.; Cañada, F.J.; Uhrig, M.L.; Cagnoni, A.J.; Manzano, V.E.; Varela, O.; Jiménez-Barbero, J.
Filiación:Chemical and Physical Biology, Centro de Investigationes BiolÒgicas, CSIC, Ramiro de Maetzu 9, 28040 Madrid, Spain
CIHIDECAR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, Pabellón 2, 1428 Buenos Aires, Argentina
Palabras clave:conformation analysis; enzyme models; glycosides; NMR spectroscopy; S ligands; Conformation analysis; Conformational selection; Enzyme models; Experimental evidence; Glycosidase inhibitors; Ground-state conformations; Molecular modeling techniques; S ligands; Chemical compounds; Escherichia coli; Glycosides; Ligands; Molecular recognition; Nuclear magnetic resonance spectroscopy; Van der Waals forces; Conformations; benzyl 3 deoxy 4 S (beta D galactopyranosyl) 4 thio beta D erythro pentopyranoside; benzyl 3 deoxy 4 S (beta D galactopyranosyl) 4 thio beta D threo pentopyranoside; benzyl-3-deoxy-4-S-(beta-D-galactopyranosyl)-4-thio-beta-D-erythro-pentopyranoside; benzyl-3-deoxy-4-S-(beta-D-galactopyranosyl)-4-thio-beta-D-threo-pentopyranoside; beta galactosidase; disaccharide; ligand; thioglycoside; article; chemical structure; chemistry; drug antagonism; enzymology; Escherichia coli; nuclear magnetic resonance spectroscopy; beta-Galactosidase; Disaccharides; Escherichia coli; Ligands; Magnetic Resonance Spectroscopy; Models, Molecular; Molecular Structure; Thioglucosides
Año:2013
Volumen:19
Número:13
Página de inicio:4262
Página de fin:4270
DOI: http://dx.doi.org/10.1002/chem.201203673
Título revista:Chemistry - A European Journal
Título revista abreviado:Chem. Eur. J.
ISSN:09476539
CODEN:CEUJE
CAS:Disaccharides; Ligands; Thioglucosides; benzyl-3-deoxy-4-S-(beta-D-galactopyranosyl)-4-thio-beta-D-erythro-pentopyranoside, 0; benzyl-3-deoxy-4-S-(beta-D-galactopyranosyl)-4-thio-beta-D-threo-pentopyranoside, 0; beta-Galactosidase, 3.2.1.23
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09476539_v19_n13_p4262_Calle

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Citas:

---------- APA ----------
Calle, L., Roldós, V., Cañada, F.J., Uhrig, M.L., Cagnoni, A.J., Manzano, V.E., Varela, O.,..., Jiménez-Barbero, J. (2013) . Escherichia coli β-galactosidase inhibitors through modifications at the aglyconic moiety: Experimental evidence of conformational distortion in the molecular recognition process. Chemistry - A European Journal, 19(13), 4262-4270.
http://dx.doi.org/10.1002/chem.201203673
---------- CHICAGO ----------
Calle, L., Roldós, V., Cañada, F.J., Uhrig, M.L., Cagnoni, A.J., Manzano, V.E., et al. "Escherichia coli β-galactosidase inhibitors through modifications at the aglyconic moiety: Experimental evidence of conformational distortion in the molecular recognition process" . Chemistry - A European Journal 19, no. 13 (2013) : 4262-4270.
http://dx.doi.org/10.1002/chem.201203673
---------- MLA ----------
Calle, L., Roldós, V., Cañada, F.J., Uhrig, M.L., Cagnoni, A.J., Manzano, V.E., et al. "Escherichia coli β-galactosidase inhibitors through modifications at the aglyconic moiety: Experimental evidence of conformational distortion in the molecular recognition process" . Chemistry - A European Journal, vol. 19, no. 13, 2013, pp. 4262-4270.
http://dx.doi.org/10.1002/chem.201203673
---------- VANCOUVER ----------
Calle, L., Roldós, V., Cañada, F.J., Uhrig, M.L., Cagnoni, A.J., Manzano, V.E., et al. Escherichia coli β-galactosidase inhibitors through modifications at the aglyconic moiety: Experimental evidence of conformational distortion in the molecular recognition process. Chem. Eur. J. 2013;19(13):4262-4270.
http://dx.doi.org/10.1002/chem.201203673