RESUMEN

The trisaccharide allyl O-(3,4-di-O-methyl-beta-D-glucopyranosyl)-(1----4)-O-(2,3-di-O-methyl-al pha-L- rhamnopyranosyl)-(1----2)-3-O-methyl-alpha-L-rhamnopyranoside was synthesized from partially methylated monosaccharide derivatives. Condensation of 1,4-di-O-acetyl-2,3-di-O-methyl-alpha-L-rhamnopyranose promoted by boron trifluoride etherate with the appropriate alcohol proceeded stereoselectively and with very high yields. Selective deacetylation and glycosylation with 2,4-di-O-acetyl-3,6-di-O-methyl-alpha-D-glucopyranosyl bromide led to a trisaccharide. The acrylamide copolymers of mono-, di-, and tri-saccharide were compared in their ability to specifically bind antibodies from leprosy patients.

Asunto(s)

Antígenos Bacterianos , Haptenos , Mycobacterium leprae/inmunología , Trisacáridos/síntesis química , Acetilación , Anticuerpos Antibacterianos/inmunología , Conformación de Carbohidratos , Secuencia de Carbohidratos , Fenómenos Químicos , Química , Glicosilación , Humanos , Lepra/inmunología , Metilación , Datos de Secuencia Molecular , Estructura Molecular , Polímeros