Porphyrin phosphonates: novel anionic receptors for saccharide recognition

Progress in biomimetic carbohydrate recognition

“…They are readily accessible and easily functionalised, while possessing large, rigid planar aromatic surface and precisely located high-affinity binding sites for metal ions. Some of these features have been exploited by Král and coworkers [64,[73][74][75][76][77][78][79] to create planar (25a-d) and macrocyclic (26a) porphyrin-based carbohydrate receptors (Fig. 5) that can be studied in aqueous solvent mixtures such as H 2 O-MeOH, 95:5.…”

“…[74]. T = 298.15 K. Errors in DH°estimated at ±10-20%.K a 's uncertain by factors of 1.3-2.0 a See Fig.…”

Interaction Between Some Monosaccharides and Aspartic Acid in Dilute Aqueous Solutions

“…It should be noted that, in aqueous solution, they exist in equilibrium of a few tautomeric forms [14,[16][17][18]. Literature data indicate that carbohydrates can exhibit α/β anomer selectivity with respect to some molecular ligands [19,20]. However, as is well known, the preponderant tautomer in the equilibrium mixture is the β-pyranose because this tautomer is the most thermodynamically favorable in water [16,18].…”

Design, Synthesis, Selective Recognition Properties and Targeted Drug Delivery Application

“…Analytical studies demonstrated significant spectral response for saccharide analytes. 15 Porphyrin phosphonates displayed stronger interaction with alkyl glucopyranoside than with galactopyranoside. Hydrophilic porphyrin phosphonates tend to bind to oligosaccharides, especially to D-(+)-maltose and α-D-lactose.…”

“…Multiple cooperative binding of the saccharide -OH and -CH groups with groups of the multifunctional receptors occurs via H-bonding with the -OH groups of binding parts of porphyrin ligands. The porphyrin ligand is constructed using the building block strategy where binding parts such as phosphonates, 15 binaphthols, 16 peptides, 17 steroids, 18 boronic acids, 19 sulfonates 20 or bile acids 5 are combined with the signaling part -a porphyrin unit, providing not only specific UV-vis and fluorescence properties but also contributing to additional binding functionality.…”