Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase

The conformational analysis of the (S) and (R) diastereoisomers of benzyl 3-deoxy-4S-(β-d-galactopyranosyl)-4-thio-β-d-threo-pentopyranoside S-oxide (1S and 1R, respectively) has been performed by using NMR spectroscopy assisted by molecular modelling methods. The results point out that sulfoxide 1S...

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Autores principales:	Colomer, J.P., Fernández de Toro, B., Cañada, F.J., Corzana, F., Jiménez Barbero, J., Canales, Á., Varela, O.
Formato:	JOUR
Materias:	Conformation analysis Glycomimetics Glycosidases Molecular recognition
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_1434193X_v2016_n30_p5117_Colomer
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	todo:paper_1434193X_v2016_n30_p5117_Colomer
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spelling	todo:paper_1434193X_v2016_n30_p5117_Colomer2023-10-03T16:14:13Z Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase Colomer, J.P. Fernández de Toro, B. Cañada, F.J. Corzana, F. Jiménez Barbero, J. Canales, Á. Varela, O. Conformation analysis Glycomimetics Glycosidases Molecular recognition The conformational analysis of the (S) and (R) diastereoisomers of benzyl 3-deoxy-4S-(β-d-galactopyranosyl)-4-thio-β-d-threo-pentopyranoside S-oxide (1S and 1R, respectively) has been performed by using NMR spectroscopy assisted by molecular modelling methods. The results point out that sulfoxide 1S and 1R display rather different conformational behaviors, 1S being significantly more flexible than 1R. Both sulfoxides have shown to be competitive inhibitors of the β-galactosidase from E. coli, although with different potencies. The key structural features of the molecular recognition process have been characterized. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_1434193X_v2016_n30_p5117_Colomer
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Conformation analysis Glycomimetics Glycosidases Molecular recognition
spellingShingle	Conformation analysis Glycomimetics Glycosidases Molecular recognition Colomer, J.P. Fernández de Toro, B. Cañada, F.J. Corzana, F. Jiménez Barbero, J. Canales, Á. Varela, O. Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase
topic_facet	Conformation analysis Glycomimetics Glycosidases Molecular recognition
description	The conformational analysis of the (S) and (R) diastereoisomers of benzyl 3-deoxy-4S-(β-d-galactopyranosyl)-4-thio-β-d-threo-pentopyranoside S-oxide (1S and 1R, respectively) has been performed by using NMR spectroscopy assisted by molecular modelling methods. The results point out that sulfoxide 1S and 1R display rather different conformational behaviors, 1S being significantly more flexible than 1R. Both sulfoxides have shown to be competitive inhibitors of the β-galactosidase from E. coli, although with different potencies. The key structural features of the molecular recognition process have been characterized. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
format	JOUR
author	Colomer, J.P. Fernández de Toro, B. Cañada, F.J. Corzana, F. Jiménez Barbero, J. Canales, Á. Varela, O.
author_facet	Colomer, J.P. Fernández de Toro, B. Cañada, F.J. Corzana, F. Jiménez Barbero, J. Canales, Á. Varela, O.
author_sort	Colomer, J.P.
title	Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase
title_short	Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase
title_full	Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase
title_fullStr	Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase
title_full_unstemmed	Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase
title_sort	diastereomeric glycosyl sulfoxides display different recognition features versus e. coli β-galactosidase
url	http://hdl.handle.net/20.500.12110/paper_1434193X_v2016_n30_p5117_Colomer
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Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase

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