Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Synthesis of 3, 6-di-O-Methylglucosyl Disaccharides with Methyl 3-(p-Hydroxyphenyl)propionate as a Linker Arm and Their Use in the Serodiagnosis of Leprosy
Tsuyoshi FUJIWARAShinzo IZUMIPatrick J. BRENNAN
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1985 年 49 巻 8 号 p. 2301-2308

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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.
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