Synthesis of dimeric aryl β-D-galactopyranosides for the evaluation of their interaction with the Erythrina cristagalli lectin

Quimica nova

Rojo, Javier¹  Meyer, Nádia Burkowski²  Alves, Ricardo José²  Figueiredo, Rute Cunha²  Prado, Maria Auxiliadôra Fontes² 

[1] Instituto de Investigaciones Químicas, Sevilla, Espanha;Universidade Federal de Minas Gerais, Belo Horizonte, Brasil

关键词: D-galactopyranose;    glycodendrimers;    Erythrina cristagalli.;   

DOI  :  10.1590/S0100-40422009000800026

学科分类：化学（综合）

来源: Sociedade Brasileira de Quimica

【 摘 要 】

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.

【 授权许可】

CC BY