Synthesis of the trisaccharide-protein conjugate of the phenolic glycolipid of Mycobacterium tuberculosis for the serodiagnosis of tuberculosis.
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.
Institute for Natural Science, Nara University, Japan.
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Fujiwara
D000942:Antigens, Bacterial; D001426:Bacterial Proteins / Q000378:metabolism*; D002240:Carbohydrate Sequence; D006017:Glycolipids / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009169:Mycobacterium tuberculosis / Q000378:metabolism; D012698:Serologic Tests; D014312:Trisaccharides / Q000138:chemical synthesis*; D014376:Tuberculosis / Q000097:blood / Q000175:diagnosis*
D000942:Antigens, Bacterial; D001426:Bacterial Proteins; D006017:Glycolipids; D006027:Glycosides; D014312:Trisaccharides; C045169:phenolic glycolipid I, Mycobacterium leprae