Journal
CARBOHYDRATE RESEARCH
Volume 346, Issue 2, Pages 348-351Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2010.11.028
Keywords
HNK-1; Bacterial glucuronylation; Sulfation
Funding
- Cluster Region Rhone-Alpes fellowship
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This work reports the synthesis and the biological validation of a trisaccharide analogue of the HNK-1 epitope. The 3-O-sulfo-beta-D-GlcpA-(1 -> 3)-beta-D-Galp-(1 -> 4)-beta-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. (C) 2010 Elsevier Ltd. All rights reserved.
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