HOMEPRODUCTSCOMPANYCONTACTFAQResearchDictionaryPharmaSign Up FREE or Login

Chemical synthesis of the trisaccharide unit of the species-specific phenolic glycolipid from Mycobacterium leprae.

Abstract
O-(3,6-Di-O-methyl-beta-D-glucopyranosyl)-(1----4)-O-(2,3-di-O-methyl- alpha-L-rhamnopyranosyl)-(1----2)-3-O-methyl-L-rhamnopyranose, the haptenic trisaccharide of the Mycobacterium leprae-specific phenolic glycolipid I (PGL-I) antigen, and related trisaccharides, were synthesized by allylation of O-2 of benzyl 4-O-benzyl-alpha-L-rhamnopyranoside using phase-transfer catalysis, methylation of the product, deallylation, and coupling to O-(2,4-di-O-acetyl-3,6-di-O-methyl-beta-D-glucopyranosyl)-(1----4)-2,3- di-O-methyl-L-rhamnopyranosyl bromide or related disaccharides. Anomeric mixtures of the trisaccharide derivatives were separated by preparative t.l.c., deacetylated, and hydrogenolyzed, to give the pure trisaccharides. It had already been demonstrated that only those trisaccharides containing an intact, terminal 3,6-di-O-methyl-beta-D-glucopyranosyl unit are effective in inhibiting the specific binding between PGL-I and anti-PGL-I immunoglobulin M antibodies in human lepromatous leprosy sera.
AuthorsT Fujiwara, G O Aspinall, S W Hunter, P J Brennan
JournalCarbohydrate research (Carbohydr Res) Vol. 163 Issue 1 Pg. 41-52 (Jun 01 1987) ISSN: 0008-6215 [Print] Netherlands
PMID3300972 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S., Research Support, U.S. Gov't, P.H.S.)
Chemical References
  • Antigen-Antibody Complex
  • Antigens, Bacterial
  • Glycolipids
  • Immunoglobulin M
  • Indicators and Reagents
  • Oligosaccharides
  • phenolic glycolipid I, Mycobacterium leprae
Topics
  • Antigen-Antibody Complex
  • Antigens, Bacterial (immunology)
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Glycolipids (immunology)
  • Humans
  • Immunoglobulin M (immunology)
  • Indicators and Reagents
  • Leprosy (immunology)
  • Mycobacterium leprae (immunology)
  • Oligosaccharides (chemical synthesis, immunology)

Join CureHunter, for free Research Interface BASIC access!

Take advantage of free CureHunter research engine access to explore the best drug and treatment options for any disease. Find out why thousands of doctors, pharma researchers and patient activists around the world use CureHunter every day.
Realize the full power of the drug-disease research graph!


Choose Username:
Email:
Password:
Verify Password:
Enter Code Shown: