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

JUAN P. COLOMER; BEATRIZ FERNÁNDEZ DE TORO; F. JAVIER CAÑADA; FRANCISCO CORZANA; JESÚS JIMÉNEZ-BARBERO; ÁNGELES CANALES ; OSCAR VARELA

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

WILEY-V C H VERLAG GMBH

Lugar: Weinheim; Año: 2016 vol. 2016 p. 5117 - 5117

1434-193X

he conformational analysis of the (S) and (R) diastereoisomersof benzyl 3-deoxy-4S-(-D-galactopyranosyl)-4-thio-beta-D-threo-pentopyranoside S-oxide (1S and 1R, respectively)has been performed by using NMR spectroscopy assistedby molecular modelling methods. The results point out thatsulfoxide 1S and 1R display rather different conformational behaviors, 1S being significantly more flexible than 1R. Bothsulfoxides have shown to be competitive inhibitors of the -galactosidase from E. coli, although with different potencies.The key structural features of the molecular recognition processhave been characterized.