Abstract
Synthetic multivalent glycoclusters show promise as anti-adhesives for the treatment of bacterial infections. Here we report the synthesis of a family of tetravalent galactose and lactose functionalised macrocycles based on the resorcin[4]arene core. The development of diastereoselective synthetic routes for the formation of lower-rim propargylated resorcin[4]arenes and their functionalistion via Cu-catalyzed azide-alkyne click chemistry is described. ELLA binding studies confirm that galactose sugar clusters are effective ligands for the PA-IL bacterial lectin of Pseudomonas aeruginosa while poor binding for the lactose-based monovalent probe and no binding could be measured for the multivalent glycoclusters was observed for the human galectin-1.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Alkynes / chemistry
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Azides / chemistry
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Calixarenes / chemical synthesis
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Calixarenes / chemistry*
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Catalysis
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Chemistry Techniques, Synthetic
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Click Chemistry
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Copper / chemistry*
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Crystallography, X-Ray
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Galactose / chemical synthesis*
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Galactose / chemistry
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Galectin 1 / antagonists & inhibitors
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Humans
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Lactose / chemical synthesis*
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Lactose / chemistry
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Lectins / chemistry*
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Lectins / pharmacology
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Ligands
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Models, Molecular
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Molecular Structure
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Phenylalanine / analogs & derivatives*
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Phenylalanine / chemical synthesis
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Phenylalanine / chemistry
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Pseudomonas aeruginosa / chemistry
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Stereoisomerism
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Structure-Activity Relationship
Substances
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Alkynes
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Azides
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Galectin 1
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Lectins
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Ligands
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resorcinarene
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Calixarenes
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Phenylalanine
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Copper
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Lactose
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Galactose