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

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
42
Issue
20
Identifiers
DOI: 10.1016/s0040-4039(01)00486-5
Disciplines
  • Chemistry
  • Design
  • Medicine

Abstract

Abstract 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.

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