Abstract
This work reports the synthesis and the biological validation of a trisaccharide analogue of the HNK-1 epitope. The 3-O-sulfo-β-d-GlcpA-(1→3)-β-d-Galp-(1→4)-β-d-Glcp-allyl has been prepared by enzymatic glucuronylation of allyl lactoside by an engineered recombinant Escherichia coli strain followed by a chemoselective sulfation. Subsequent covalent attachment of the ozone-oxidised trisaccharide to bovine serum albumin provided a neo-glycoconjugate, which has been interrogated with antibodies specific to the human natural killer carbohydrate epitope HNK-1. ELISA assays confirmed the absolute requirement of the sulfate group for protein recognition and the potential application of this synthetic oligosaccharide as HNK-1 surrogate.
2010 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Allyl Compounds / chemistry
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Allyl Compounds / immunology
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Allyl Compounds / metabolism*
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Brain / immunology
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CD57 Antigens / biosynthesis*
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CD57 Antigens / chemistry
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CD57 Antigens / immunology
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Carbohydrate Sequence
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Enzyme-Linked Immunosorbent Assay
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Escherichia coli / enzymology*
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Escherichia coli / genetics
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Humans
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Immunodominant Epitopes / biosynthesis*
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Immunodominant Epitopes / chemistry
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Immunodominant Epitopes / immunology
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Molecular Sequence Data
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Oligosaccharides / biosynthesis*
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Oligosaccharides / chemistry
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Oligosaccharides / immunology
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Serum Albumin, Bovine / chemistry
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Trisaccharides / biosynthesis*
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Trisaccharides / chemistry
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Trisaccharides / immunology
Substances
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Allyl Compounds
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CD57 Antigens
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Immunodominant Epitopes
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Oligosaccharides
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Trisaccharides
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Serum Albumin, Bovine