Synthesis of multivalent glycoclusters bearing thiodigalactoside analogues

ALEJANDRO J. CAGNONI; OSCAR VARELA; JOSÉ KOVENSKY; MARÍA LAURA UHRIG

Madrid

Simposio; 26th International Carbohydrate Symposium; 2012

International Carbohydrate Organization

As part of our ongoing project on the synthesis of multivalent glycoclusters compatible with biological media, we describe here the synthesis of a new family of hydrolytically stable glycoconjugates. The topology of the galectin carbohydrate-binding site has been deeply studied and the specific interactions with the hydroxyl groups of its natural ligand, LacNAc,  are well known. Thiodigalactoside has been shown to bind to galectins with about the same affinity as LacNAc2 thus, we have designed the thiodisaccharide analogue 2 as a stable recognition element (RE) of the lectin.