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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
- Source :
- Agricultural and Biological Chemistry. 49:2301-2308
- Publication Year :
- 1985
- Publisher :
- Oxford University Press (OUP), 1985.
-
Abstract
- The disaccharide, 2,3-di-O-methyl-4-O-(3,6-di-O-methyl-β-d-glucopyranosyl)-l-rhamno-pyranose, 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.
- Subjects :
- chemistry.chemical_classification
biology
Stereochemistry
Disaccharide
Glycoside
biology.organism_classification
Chemical synthesis
General Biochemistry, Genetics and Molecular Biology
chemistry.chemical_compound
Glycolipid
chemistry
Bromide
Propionate
General Agricultural and Biological Sciences
Linker
Mycobacterium leprae
Subjects
Details
- ISSN :
- 18811280 and 00021369
- Volume :
- 49
- Database :
- OpenAIRE
- Journal :
- Agricultural and Biological Chemistry
- Accession number :
- edsair.doi.dedup.....bd7ed5426b4a1af1f976026676e5dc2e