α-Galactose based neoglycopeptides. Inhibition of verotoxin binding to globotriosylceramide

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DOIResolve DOI: http://doi.org/10.1016/S0968-0896(99)00226-6
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TypeArticle
Journal titleBioorganic & Medicinal Chemistry
Volume7
Issue12
Pages28232833; # of pages: 11
Subjectcarbohydrate-protein interactions; globotriosylceramide mimics; glycomimetics; glycopeptides; Neoglycopeptides; verotoxin
AbstractSolution and solid phase strategies for the synthesis of α-galactose based neoglycopeptide derivatives Figure 2, Figure 3, Figure 3, Scheme 3 and Scheme 4 were developed. Neoglycopeptides generated were tested for the inhibition of verotoxin binding to globotriosylceramide (Gb3) using ELISA. Among all of the compounds tested, only the lipid derivatives of neoglycopeptides, Figure 3 and Scheme 4 and Figure 3 and Scheme 4 were found to be inhibitors, IC50=2.0 mM (Figure 3 and Scheme 4) and 0.2 mM (Figure 3 and Scheme 4). All of the inhibitors (Figure 3 and Scheme 4) have a similar branching of the two α-galactosyl units at the N-terminal glycine residue of a short peptide and a lipid moiety attached at the C-terminal site. Both of these factors seem to be crucial for the inhibition. It is interesting to note that the inhibitors have only a portion of the natural trisaccharide ligand. The secondary groups either may contribute in sub-site oriented interactions with the protein receptors or may mimic the internal sugar units of the cell-surface ligand, Gb3.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada; NRC Institute for Microstructural Sciences
Peer reviewedNo
NPARC number12338102
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Record identifierc3fbb204-5ac0-4ae0-98af-eac920a6c47e
Record created2009-09-10
Record modified2016-05-09
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