The rational design of an iminosugar inhibitor able to mimic substrate distortion occurring during retaining-cellulase hydrolysis

This paper reports the rational design, synthesis and biochemical evaluation of a new type of cellulase inhibitor. This isofagomine isomer analogous to the β- l-idopyranose linked to a glucosidic unit by a methylenic bond is able to mimic the pseudo-axial orientation of the ‘aglycon’ observed in the X-ray structure of a non-hydrolyzable thiooligosaccharide/cellulase complex. Graphic