Synthesis and NMR analysis of 13C-labeled oligosaccharides corresponding to the major glycolipid from Mycobacterium leprae.

Wu, X; Mariño-Albernas, J R; Auzanneau, F I; Verez-Bencomo, V; Pinto, B M

Wu, X; Mariño-Albernas, J R; Auzanneau, F I; Verez-Bencomo, V; Pinto, B M.

Afiliación

Wu X; Department of Chemistry, Simon Fraser University, Burnaby, B.C., Canada.

Carbohydr Res ; 306(4): 493-503, 1998 Feb.

Article en En | MEDLINE | ID: mdl-9679274

RESUMEN

An improved synthesis of propyl 4-O-(3,6-di-O-methyl- beta-D-glucopyranosyl)-2,3-di-O-methyl-alpha-L-rhamnopyranoside, a disaccharide corresponding to the phenolic glycolipid of Mycobacterium leprae using a trichloroacetimidate as a glycosyl donor is described. The synthetic strategy is also applied to the preparation of three corresponding disaccharide analogues containing 13C-labeled methyl groups. The preparation of the trisaccharide, propyl 2-O-[4-O-(3,6-di-O-methyl-beta-D-glucopyranosyl)-2,3-di-O-methyl-alpha-L - rhamnopyranosyl]-3-O-methyl-alpha-L-rhamnopyranoside is also reported. The di- and tri-saccharides were characterized by 1H and 13C NMR spectroscopy.

Asunto(s)

Antígenos Bacterianos/química; Disacáridos/síntesis química; Glucolípidos/síntesis química; Mycobacterium leprae/química; Trisacáridos/síntesis química; Secuencia de Carbohidratos; Isótopos de Carbono; Haptenos/química; Marcaje Isotópico; Datos de Secuencia Molecular; Mycobacterium leprae/inmunología; Resonancia Magnética Nuclear Biomolecular

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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Trisacáridos / Glucolípidos / Disacáridos / Mycobacterium leprae / Antígenos Bacterianos Idioma: En Revista: Carbohydr Res Año: 1998 Tipo del documento: Article País de afiliación: Canadá Pais de publicación: Países Bajos

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