Synthesis of the trisaccharide-protein conjugate of the phenolic glycolipid of Mycobacterium tuberculosis for the serodiagnosis of tuberculosis.

Article abstract of DOI:10.1271/bbb1961.55.2123

The trisaccharide segment of the phenolic glycolipid (PGL) of Mycobacterium tuberculosis, 2-O-methyl-3-O-[3-O-(2,3,4-tri-O-methyl-alpha-L-fucopyranosyl)-alpha-L- rhamnopyranosyl]-alpha-L-rhamnopyranose, was synthesized in the form of the p-(2-methoxycarbonylethyl)phenyl glycoside by a stepwise condensation. 2,4-Di-O-benzyl-3-O-acetyl-alpha-L-rhamnopyranosyl chloride was coupled to p-(2-methoxycarbonylethyl)phenyl 4-O-benzyl-2-O-methyl-alpha-L-rhamnopyranoside in the presence of silver triflate, and 2,3,4-tri-O-methyl-alpha-L-rhamnopyranosyl chloride was then coupled to the deacetylated disaccharide by the same procedure. The trisaccharide was deblocked and coupled to BSA, giving the neoglycoconjugate TB-NT-P-BSA. TB-NT-P-BSA showed its possibility as a useful tool for the serodiagnosis of tuberculosis.