Síntese de β-D-galactopiranosídeos de arila diméricos para avaliação de sua interação com a lectina de Erythrina cristagalli Synthesis of dimeric aryl β-D-galactopyranosides for the evaluation of their interaction with the Erythrina cristagalli lectin

Abstract

The synthesis of two new D-galactose-based dimers having a 1,4-butanediamine spacer is reported aiming at the evaluation of their interaction with the Erythrina cristagalli lectin. The title compounds were prepared in four and five steps from 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside bromide, in 20 % and 15 % overall yield, respectively, using the Doebner modification of the Koenavenagel reaction as the key sep. The lectin-carbohydrate interaction could be evaluated for only one dimer, due to solubility problems. A twofold enhancement of affinity was observed, compared to the corresponding monovalent ligand.

Keywords

• D-galactopyranose
• glycodendrimers
• Erythrina cristagalli