1995
DOI: 10.1039/c39950001257
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Molecular recognition of carbohydrates by functionalized zinc porphyrins

Abstract: A trifunctional porphyrin host ~cis-5,15-bis(8-quinolyl)porphyrinatoIzinc 1 exhibits a marked affinity for octyl p-o-glucopyranoside 12 in CHC13 with an association constant of 41 400 dm3 mol-1; solvent effects on the binding are compared with those for [cis-5,15-bis(2,7-dihydroxy-1-naphthyl)porphyrinato]zinc 3.

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Cited by 23 publications
(14 citation statements)
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“…[3c] This motif was combined again with H-bonding sites in the ªU-shapedº receptors 49 ± 51, by Mizutani, Ogoshi et al With octyl b-d-glucoside (12) in CHCl 3 , these molecules were able to form complexes with K a 180, 2090, and 41 400 m À1 , respectively. [29] Receptor 50 (but not 51) once more increased in potency on addition of a small quantity of hydroxylic solvent.…”
Section: Valleys Bowls Rings and Cages: Further Architectures Withmentioning
confidence: 94%
“…[3c] This motif was combined again with H-bonding sites in the ªU-shapedº receptors 49 ± 51, by Mizutani, Ogoshi et al With octyl b-d-glucoside (12) in CHCl 3 , these molecules were able to form complexes with K a 180, 2090, and 41 400 m À1 , respectively. [29] Receptor 50 (but not 51) once more increased in potency on addition of a small quantity of hydroxylic solvent.…”
Section: Valleys Bowls Rings and Cages: Further Architectures Withmentioning
confidence: 94%
“…Zinc porphyrins are known to bind to a variety of diols, including many saccharides, such as glucosides and mannosides (Bonar-Law and Sanders, 1995;Mizutani et al, 1995). Resorcinarenes have also been reported to be able to extract some sugars (Tanaka et al, 1989).…”
Section: ) Glucose/fructose Separationmentioning
confidence: 99%
“…For example, boronic acid porphyrins have been used for sugar sensing [96][97][98][99][100][101][102][103][104][105] , discrimination of sugars [106,107] , and have been used to control sugar-DNA interactions [108] . Boronic acid porphyrins have also been employed in glycosylated steroid sensing [109] and the detection of carbohydrates on the surface of cells using a photochemical approach [110] .…”
Section: Porphyrin Carbohydrate Interactionsmentioning
confidence: 99%