Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β-Galactosidase
- Colomer, J.P. 2
- Fernández de Toro, B. 4
- Cañada, F.J. 4
- Corzana, F. 5
- Jiménez Barbero, J. 137
- Canales, Á. 6
- Varela, Oscar . 2
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1
Centro de Investigación Cooperativa en Biotecnología
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Centro de Investigación Cooperativa en Biotecnología
Zamudio, España
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2
Universidad de Buenos Aires
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3
Universidad del País Vasco/Euskal Herriko Unibertsitatea
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Universidad del País Vasco/Euskal Herriko Unibertsitatea
Lejona, España
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4
Centro de Investigaciones Biológicas
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5
Universidad de La Rioja
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6
Universidad Complutense de Madrid
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- 7 IKERBASQUE, Basque Foundation for Science, Bilbao, Spain
ISSN: 1434-193X
Année de publication: 2016
Volumen: 2016
Número: 30
Pages: 5117-5122
Type: Article
D'autres publications dans: European Journal of Organic Chemistry
Résumé
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