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Chemical synthesis of an artifical antigen containing the trisaccharide hapten of mycobacterium leprae

✍ Scribed by J. Mariño-Albernas; Vicente Verez-Bencomo; L. Gonzalez-Rodriguez; C.S. Perez-Martinez; E.Gonzalez-Abreu Castell; A. Gonzalez-Segredo

Publisher: Elsevier Science
Year: 1988
Tongue: English
Weight: 502 KB
Volume: 183
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(88)84072-2

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✦ Synopsis

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.

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