Abstract
A systematic study of the binding of carbohydrates by functionalized zinc porphyrins indicated that [5, 15-bis(8-quinolyl)porphyrinato]zinc(II) (1) showed marked affinity for octyl glucoside and mannoside in CHCl3 (−ΔG° = 4.5−6.3 kcal mol-1). Analysis of the complexation-induced shifts of the carbohydrate OH protons in the 1H NMR revealed that receptor 1 bound the 4-OH group of mannoside and glucoside by coordination to the zinc and the 6-OH and 3-OH groups by hydrogen bonding to the quinolyl nitrogen atoms. These NMR results and comparison of binding affinity with reference receptors and ligands indicated that receptor 1 recognized the trans,trans-1,2-dihydroxy-3-(hydroxymethyl) moiety of carbohydrates by the combination of Lewis acid (zinc) and Lewis bases (quinolyl nitrogens). Poor affinities of 1 to octyl galactosides and octyl 2-O-methyl-α-mannoside were ascribed to neighboring group effects, where a neighboring group in ligands not directly involved in the receptor−ligand interactions had considerab...
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