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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" (2016) European Journal of Organic Chemistry. 2016(30):5117-5122
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Abstract:

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

Registro:

Documento: Artículo
Título:Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase
Autor:Colomer, J.P.; Fernández de Toro, B.; Cañada, F.J.; Corzana, F.; Jiménez Barbero, J.; Canales, Á.; Varela, O.
Filiación:CIHIDECAR-CONICET-UBA, Department of Organic Chemistry, Exact and Natural Sciences Faculty, University of Buenos Aires, Ciudad Universitaria, Pab. II, Buenos Aires, 1428, Argentina
Department of Chemical and Physical Biology, Biological Research Center, Spanish National Research Council (CIB-CSIC), Ramiro de Maeztu 9, Madrid, 28040, Spain
Department of Chemistry, Research Center of Chemistry Synthesis, University of La Rioja, Madre de Dios 53, Logroño, 26006, Spain
CIC bioGUNE, Bizkaia Science and Technology Park, Building 801A, Derio, 48160, Spain
IKERBASQUE, Basque Foundation for Science, Bilbao, 48009, Spain
Departament of Organic Chemistry II, Faculty of Science & Technology, University of the Basque Country, Leioa, 48940, Spain
Department of Organic Chemistry I, Chemical Sciences Faculty, Complutense University, Madrid, 28040, Spain
Palabras clave:Conformation analysis; Glycomimetics; Glycosidases; Molecular recognition
Año:2016
Volumen:2016
Número:30
Página de inicio:5117
Página de fin:5122
DOI: http://dx.doi.org/10.1002/ejoc.201600835
Título revista:European Journal of Organic Chemistry
Título revista abreviado:Eur. J. Org. Chem.
ISSN:1434193X
CODEN:EJOCF
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1434193X_v2016_n30_p5117_Colomer

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Citas:

---------- APA ----------
Colomer, J.P., Fernández de Toro, B., Cañada, F.J., Corzana, F., Jiménez Barbero, J., Canales, Á. & Varela, O. (2016) . Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase. European Journal of Organic Chemistry, 2016(30), 5117-5122.
http://dx.doi.org/10.1002/ejoc.201600835
---------- CHICAGO ----------
Colomer, J.P., Fernández de Toro, B., Cañada, F.J., Corzana, F., Jiménez Barbero, J., Canales, Á., et al. "Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase" . European Journal of Organic Chemistry 2016, no. 30 (2016) : 5117-5122.
http://dx.doi.org/10.1002/ejoc.201600835
---------- MLA ----------
Colomer, J.P., Fernández de Toro, B., Cañada, F.J., Corzana, F., Jiménez Barbero, J., Canales, Á., et al. "Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase" . European Journal of Organic Chemistry, vol. 2016, no. 30, 2016, pp. 5117-5122.
http://dx.doi.org/10.1002/ejoc.201600835
---------- VANCOUVER ----------
Colomer, J.P., Fernández de Toro, B., Cañada, F.J., Corzana, F., Jiménez Barbero, J., Canales, Á., et al. Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase. Eur. J. Org. Chem. 2016;2016(30):5117-5122.
http://dx.doi.org/10.1002/ejoc.201600835