Multivalent iminosugars to modulate affinity and selectivity for glycosidases.
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.
Diot
Jennifer
J
Laboratoire des Glucides UMR CNRS 6219, Institut de Chimie de Picardie, Faculté des Sciences, Université de Picardie Jules Verne, 33 rue Saint-Leu, 80039 Amiens Cedex 1, France.
García-Moreno
M Isabel
MI
Gouin
Sébastien G
SG
Ortiz Mellet
Carmen
C
Haupt
Karsten
K
Kovensky
José
J
D017485:1-Deoxynojirimycin / Q000737:chemistry; D005944:Glucosamine / Q000031:analogs & derivatives / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors* / Q000737:chemistry; D050111:Imino Sugars / Q000737:chemistry*; D013329:Structure-Activity Relationship
D050111:Imino Sugars; C501633:deoxynojirimycine; D017485:1-Deoxynojirimycin; D006026:Glycoside Hydrolases; D005944:Glucosamine