Fucosylated Pentaerythrityl Phosphodiester Oligomers (PePOs): Automated Synthesis of DNA-Based Glycoclusters and Binding to Pseudomonas aeruginosa Lectin (PA-IIL)
Bioconjugate Chemistry2007Vol. 18(5), pp. 1637–1643
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F. Morvan, Albert Meyer, A.M. Jochum, Charles Sabin, Yann Chevolot, Anne Imberty, Jean‐Pierre Praly, Jean‐Jacques Vasseur, Éliane Souteyrand, Sébastien Vidal
Abstract
The synthesis of propargylated pentaerythrityl phosphodiester oligomers (PePOs) was achieved using a DNA synthesizer with a bis-propargylated pentaerythritol-based phosphoramidite. An azido fucose derivative was reacted under "click" chemistry conditions activated by microwaves to construct a series of glycosylated PePOs bearing 4, 6, 8, and 10 L-fucose residues. Binding to the fucose-specific bacterial lectin (PA-IIL) was determined for the fucosylated PePOs through an enzyme-linked lectin amplification competition assay. The IC50 values measured are 10-20 times better than for monovalent l-fucose and denotate for a "macromolecular" effect rather than a "cluster" effect.
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