Abstract
The blood group P1 antigenic trisaccharide (3), which is the receptor-binding ligand of Shiga-like toxins, is synthesized in a spacer-equipped form (32) from 2-(trimethylsilyl)ethyl glucoside 5 and the 1-thiogalactoside building blocks 10 and 22 in a stereocontrolled, stepwise fashion. Covalent attachment of 32 to hydrazine group-containing agarose gel by reductive amination provided the P1 trisaccharide-containing affinity sorbent which was used for preparative scale isolation of subunit B of Shiga toxin.
MeSH terms
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Automation
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Bacterial Toxins / chemistry
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Bacterial Toxins / isolation & purification*
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Carbohydrate Conformation
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Carbohydrate Sequence
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Chromatography, Affinity / methods
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Enterotoxins / chemistry
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Enterotoxins / isolation & purification
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Gels
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Glycosides
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Humans
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Indicators and Reagents
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Magnetic Resonance Spectroscopy
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Molecular Sequence Data
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P Blood-Group System
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Sepharose
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Shiga Toxins
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Trisaccharides / chemical synthesis*
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Trisaccharides / chemistry
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Vibrio cholerae
Substances
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Bacterial Toxins
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Enterotoxins
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Gels
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Glycosides
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Indicators and Reagents
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P Blood-Group System
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Shiga Toxins
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Trisaccharides
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Sepharose