Fucosylated pentaerythrityl phosphodiester oligomers (PePOs): automated synthesis of DNA-based glycoclusters and binding to Pseudomonas aeruginosa lectin (PA-IIL).
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.
Morvan
François
F
Institut des Biomolécules Max Mousseron, UMR 5247 CNRS - Université Montpellier I - Université Montpellier II, LACAN, CC008, Place E. Bataillon, 34095 Montpellier Cedex 5, France.
Meyer
Albert
A
Jochum
Anne
A
Sabin
Charles
C
Chevolot
Yann
Y
Imberty
Anne
A
Praly
Jean-Pierre
JP
Vasseur
Jean-Jacques
JJ
Souteyrand
Eliane
E
Vidal
Sébastien
S
D001386:Azides / Q000737:chemistry; D001665:Binding Sites; D004247:DNA / Q000737:chemistry*; D005643:Fucose / Q000737:chemistry*; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000378:metabolism*; D037102:Lectins / Q000378:metabolism*; D008956:Models, Chemical; D021141:Nucleic Acid Amplification Techniques; D010755:Organophosphates / Q000138:chemical synthesis; D009943:Organophosphorus Compounds / Q000737:chemistry; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D011409:Propylene Glycols / Q000737:chemistry; D011550:Pseudomonas aeruginosa / Q000378:metabolism*
D001386:Azides; D006001:Glycoconjugates; D037102:Lectins; D010755:Organophosphates; D009943:Organophosphorus Compounds; D011409:Propylene Glycols; C434331:phosphoramidite; D005643:Fucose; D004247:DNA; D010293:Pargyline; C008783:pentaerythritol