Abstract
The disaccharide, 2, 3-di-O-methyl-4-O-(3, 6-di-O-methyl-β-D-glucopyranosyl)-L-rhamnopyranose, the distal segment of phenolic glycolipid I, that is a specific antigen from Mycobacterium leprae, and some related disaccharides were synthesised as the glycosides of methyl 3-(p-hydroxyphenyl)propionate. The methyl 3-(p-hydroxyphenyl)propionate was coupled with 2, 3, 4-tri-O-acetyl-L-rhamnosyl bromide, deacetylated, acetonated, coupled with 2, 4, 6-tri-O-acetyl-3-O-methyl-D-glucosyl bromide, and converted into a variety of p-(2-methoxycarbonylethyl)phenyl 4-O-(3, 6-di-O-methyl-D-glucopyranosyl)-containing disaccharides that are amenable to ready conjugation with protein carriers, thereby providing neo-glycoconjugates for the specific serodiagnosis of leprosy.
