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

Autor: Rute Cunha Figueiredo, Nádia Burkowski Meyer, Maria Auxiliadôra Fontes Prado, Ricardo José Alves, Javier Rojo
Jazyk: English<br />Spanish; Castilian<br />Portuguese
Rok vydání: 2009
Předmět:
Zdroj: Química Nova, Vol 32, Iss 8, Pp 2128-2132 (2009)
Druh dokumentu: article
ISSN: 0100-4042
1678-7064
DOI: 10.1590/S0100-40422009000800026
Popis: 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.
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