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Synthesis of Galactoclusters by Metal-Free Thiol 'Click Chemistry' and Their Binding Affinities forPseudomonas aeruginosaLectin LecA
- Source :
- European Journal of Organic Chemistry. 2014:7621-7630
- Publication Year :
- 2014
- Publisher :
- Wiley, 2014.
-
Abstract
- Mannose-centered galactoclusters specific for lectin I of Pseudomonas aeruginosa (LecA) were synthesised by a combination of phosphoramidite chemistry and metal-free thiol click chemistry (i.e., thiol addition to acrylamide or nucleophilic displacement of bromine in a bromoacetamide group by a thiol function). These thiol click reactions were performed with microwave assistance in the presence of Et3N and with use of a reducing agent to avoid disulfide formation. Nine tetravalent galactoclusters containing different linkers (aliphatic, oligoethyleneglycol or aromatic) were synthesised with a DNA tag. Their binding to LecA was monitored in a DNA-based glycoarray and compared with that of a galactocluster synthesised by copper-catalyzed azide–alkyne cycloaddition. The results indicated stronger binding of all galactoclusters relative to the monovalent galactoside but slightly weaker binding than that shown by the galactocluster incorporating a triazole ring, due to a favourable interaction of the latter with proline 51 of LecA.
- Subjects :
- chemistry.chemical_classification
Phosphoramidite
010405 organic chemistry
Reducing agent
Organic Chemistry
Triazole
010402 general chemistry
01 natural sciences
Galactoside
Combinatorial chemistry
Cycloaddition
0104 chemical sciences
chemistry.chemical_compound
chemistry
Nucleophile
Thiol
Click chemistry
Organic chemistry
Physical and Theoretical Chemistry
Subjects
Details
- ISSN :
- 1434193X
- Volume :
- 2014
- Database :
- OpenAIRE
- Journal :
- European Journal of Organic Chemistry
- Accession number :
- edsair.doi...........526c4665ec1e921e4d19ae1d22c078bb