Chemical synthesis of an artifical antigen containing the trisaccharide hapten of mycobacterium leprae
1988; Elsevier BV; Volume: 183; Issue: 2 Linguagem: Inglês
10.1016/0008-6215(88)84072-2
ISSN1873-426X
AutoresJosé-R. Marino-Albernas, Vicente Vérez-Bencomo, Larissa Linnette González-Rodríguez, Carlos Pérez–Martínez, E.Gonzalez-Abreu Castell, A. Gonzalez-Segredo,
Tópico(s)Biochemical and Molecular Research
ResumoThe 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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