Synthesis of the repeating unit of the O-specific polysaccharide of Shigella sonnei and quantitation of its serologic activity

The chemical synthesis of the zwitterionic disaccharide 2 is described that corresponds to the repeating unit of the O-specific polysaccharide (1) of the gram-negative human pathogen Shigella sonnei. Passive hemolysis inhibition tests using a hyperimmune rabbit serum raised against S. sonnei showed...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2000-01, Vol.10 (1), p.19-21
Main Authors: TOTH, A, MEDGYES, A, BAJZA, I, LIPTAK, A, BATTA, G, KONTROHR, T, PETERFFY, K, POZSGAY, V
Format: Article
Language:English
Subjects:
Animals
Bacteriology
Biological and medical sciences
Complement System Proteins - immunology
Disaccharides - chemical synthesis
Disaccharides - immunology
Erythrocytes - immunology
Fundamental and applied biological sciences. Psychology
Galactose - analogs & derivatives
Galactose - chemistry
Guinea Pigs
Hemolysis
Lipopolysaccharides - immunology
Microbiology
Monosaccharides - chemistry
Monosaccharides - immunology
Nuclear Magnetic Resonance, Biomolecular
O Antigens - chemistry
O Antigens - immunology
O Antigens - metabolism
Rabbits
Sheep
Shigella sonnei - immunology
Shigella sonnei - metabolism
Stereoisomerism
Uronic Acids - chemistry
Vaccines, antisera, therapeutical immunoglobulins and monoclonal antibodies
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Summary:The chemical synthesis of the zwitterionic disaccharide 2 is described that corresponds to the repeating unit of the O-specific polysaccharide (1) of the gram-negative human pathogen Shigella sonnei. Passive hemolysis inhibition tests using a hyperimmune rabbit serum raised against S. sonnei showed that the serologic activity of the disaccharide 2 is nearly 2- to 3-fold higher than those of its component monosaccharides. NMR data of 2 are in support of the proposed structure of the O-specific polysaccharide.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(99)00585-5