Chemical synthesis of an artificial antigen containing the trisaccharide hapten of Mycobacterium leprae.

Autor: Mariño-Albernas J; Laboratory for Carbohydrate Chemistry, Facultad de Quimica, Universidad de la Habana, Cuba., Verez-Bencomo V, Gonzalez-Rodriguez L, Perez-Martinez CS, Gonzalez-Abreu Castell E, Gonzalez-Segredo A
Jazyk: angličtina
Zdroj: Carbohydrate research [Carbohydr Res] 1988 Dec 01; Vol. 183 (2), pp. 175-82.
DOI: 10.1016/0008-6215(88)84072-2
Abstrakt: 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.
Databáze: MEDLINE