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Diastereomeric Glycosyl Sulfoxides Display Different Recognition Features versus E. coli β‐Galactosidase
Author(s) -
Colomer Juan P.,
Fernández de Toro Beatriz,
Cañada F. Javier,
Corzana Francisco,
Jiménez Barbero Jesús,
Canales Ángeles,
Varela Oscar
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600835
Subject(s) - chemistry , diastereomer , sulfoxide , stereochemistry , glycosyl , thio , molecular recognition , nuclear magnetic resonance spectroscopy , molecule , organic chemistry
The conformational analysis of the ( S ) and ( R ) diastereoisomers of benzyl 3‐deoxy‐4 S ‐(β‐ d ‐galactopyranosyl)‐4‐thio‐β‐ d ‐ threo ‐pentopyranoside S ‐oxide ( 1 S and 1 R , respectively) has been performed by using NMR spectroscopy assisted by molecular modelling methods. The results point out that sulfoxide 1 S and 1 R display rather different conformational behaviors, 1 S being significantly more flexible than 1 R . 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.