Synthesis of the Neoglycoconjugates of Phenolic Glycolipid-related Trisaccharides for the Serodiagnosis of Leprosy

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概要

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• The trisaccharide segment of the phenolic glycolipid I of Mycobacterium leprae was synthesized effectively in the form of p-(2-methoxycarbonylethyl)phenyl glycoside by the condensation of p-(2-methoxycarbonylethyl)phenyl 4-O-benzyl-3-O-methyl-α-L-rhamnopyranoside and 2, 3-di-O-methyl-4-O-(2, 4-di-O-acetyl-3, 6-di-O-methyl-β-D-glucopyranosyl)-α-L-rhamnopyranosyl chloride in the presence of silver triflate and 1, 1, 3, 3-tetra-N-methylurea, and subsequent selective deprotection. This was then coupled to BSA by the acyl azide method, giving NT-P-BSA. The NT-P-BSA showed very high reactivity and specificity to leprosy sera. The trisaccharide-BSA conjugate with a β-linked rhamnosylrhamnose unit (βT-P-BSA) was also synthesized.

• 社団法人 日本農芸化学会の論文

著者

• Izumi Shinzo

  Leprosy Study Group - Institute Of Tropical Disease Airlangga University

• FUJIWARA Tsuyoshi

  Laboratory of Chemistry, Institute for Natural Science, Nara University

• IZUMI Shinzo

  Leprosy Research Laboratory, Department of Dermatology, Faculty of Medicine, Kyoto University

関連論文

• GENOTYPING ANALYSIS BY TTC REPEAT DIVERSITY OF M. leprae CLINICAL ISOLATES AND HOUSEHOLD CONTACTS IN LEPROSY ENDEMIC AREA (Genotyping study in Sampang, East Java Province, Indonesia)
• CORRELATION BETWEEN THE SERO-POSITIVITY LEVEL AND NEW CASE DETECTION RATE (NCDR) IN SOME LEPROSY ENDEMIC AREAS OF INDONESIA
• Synthesis of the Neoglycoconjugates of Phenolic Glycolipid-related Trisaccharides for the Serodiagnosis of Leprosy
• 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

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