Chemical synthesis of an artificial antigen containing the trisaccharide hapten of Mycobacterium leprae.
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.
Mariño-Albernas
J
J
Laboratory for Carbohydrate Chemistry, Facultad de Quimica, Universidad de la Habana, Cuba.
Verez-Bencomo
V
V
Gonzalez-Rodriguez
L
L
Perez-Martinez
C S
CS
Gonzalez-Abreu Castell
E
E
Gonzalez-Segredo
A
A
D000107:Acetylation; D000907:Antibodies, Bacterial / Q000276:immunology; D000942:Antigens, Bacterial; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D055598:Chemical Phenomena; D002621:Chemistry; D006031:Glycosylation; D006241:Haptens; D006801:Humans; D007918:Leprosy / Q000276:immunology; D008745:Methylation; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009166:Mycobacterium leprae / Q000276:immunology*; D011108:Polymers; D014312:Trisaccharides / Q000138:chemical synthesis*
D000907:Antibodies, Bacterial; D000942:Antigens, Bacterial; D006241:Haptens; D011108:Polymers; D014312:Trisaccharides