01799nas a2200397   4500000000100000008004100001260001600042653001600058653002600074653002400100653003000124653002600154653002300180653001400203653001800217653001200235653001100247653001200258653001600270653002800286653002400314653002500338653001300363653001900376100002300395700002000418700002500438700002300463700002900486700002300515245010900538300001100647490000800658520072100666022001401387       1988                            d  c1988 Dec 0110aAcetylation10aAntibodies, Bacterial10aAntigens, Bacterial10aCarbohydrate Conformation10aCarbohydrate Sequence10aChemical Phenomena10aChemistry10aGlycosylation10aHaptens10aHumans10aleprosy10aMethylation10aMolecular Sequence Data10aMolecular Structure10aMycobacterium leprae10aPolymers10aTrisaccharides1 aMariño-Albernas J1 aVerez-Bencomo V1 aGonzalez-Rodriguez L1 aPerez-Martinez C S1 aGonzalez-Abreu Castell E1 aGonzalez-Segredo A00aChemical synthesis of an artificial antigen containing the trisaccharide hapten of Mycobacterium leprae.  a175-820 v1833 a<p>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.</p>  a0008-6215