@article{10360, keywords = {Acetylation, Antibodies, Bacterial, Antigens, Bacterial, Carbohydrate Conformation, Carbohydrate Sequence, Chemical Phenomena, Chemistry, Glycosylation, Haptens, Humans, leprosy, Methylation, Molecular Sequence Data, Molecular Structure, Mycobacterium leprae, Polymers, Trisaccharides}, author = {MariƱo-Albernas J and Verez-Bencomo V and Gonzalez-Rodriguez L and Perez-Martinez C S and Gonzalez-Abreu Castell E and Gonzalez-Segredo A}, title = {Chemical synthesis of an artificial antigen containing the trisaccharide hapten of Mycobacterium leprae.}, abstract = {

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.

}, year = {1988}, journal = {Carbohydrate research}, volume = {183}, pages = {175-82}, month = {1988 Dec 01}, issn = {0008-6215}, doi = {10.1016/0008-6215(88)84072-2}, language = {eng}, }