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Issue 2, 2009
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Multivalent iminosugars to modulate affinity and selectivity for glycosidases†

Jennifer Diot,a   M. Isabel García-Moreno,b   Sébastien G. Gouin,*a   Carmen Ortiz Mellet,b   Karsten Hauptc  and  José Kovensky*a  
Author affiliations

* Corresponding authors

a Laboratoire des Glucides UMR CNRS 6219, Institut de Chimie de Picardie, Faculté des Sciences, Université de Picardie Jules Verne, 33 rue Saint-Leu, Amiens Cedex 1, France
E-mail: sebastien.gouin@u-picardie.fr, jose.kovensky@u-picardie.fr
Fax: +33 03 22 82 75 60
Tel: +33 (0)3 22 82 75 69

b Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Profesor García González 1, Sevilla, Spain

c Laboratoire Génie Enzymatique et Cellulaire, UMR CNRS -6022, Université de Technologie de Compiègne BP 20205, Compiègne Cedex, France

Abstract

A series of mono-, di- and tri-valent iminosugars based on oligoethylene scaffolds and N-substituted deoxynojirymicin epitopes have been synthesized by “click chemistry” to study the effect of multivalency on glycosidase inhibition. Biological evaluation evidenced differences in the inhibition trends as a function of the enzyme nature. The results demonstrate that multivalency can be used in some case to modulate both the affinity and the selectivity of glycosidase inhibition.

Graphical abstract: Multivalent iminosugars to modulate affinity and selectivity for glycosidases

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Article information

https://doi.org/10.1039/B815408B
Submitted
03 Sep 2008
Accepted
17 Oct 2008
First published
18 Nov 2008
Org. Biomol. Chem., 2009,7, 357-363
Article type
Paper
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Multivalent iminosugars to modulate affinity and selectivity for glycosidases

J. Diot, M. I. García-Moreno, S. G. Gouin, C. Ortiz Mellet, K. Haupt and J. Kovensky, Org. Biomol. Chem., 2009, 7, 357
DOI: 10.1039/B815408B

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