1,1'-Binaphthyl-substituted macrocycles as receptors for saccharide recognition.
The preparation of receptors for saccharide recognition in a natural environment has been an unmet goal for a long time. We present herein the synthesis and binding properties of (R,S)-1,1'-binaphthyl-substituted macrocycles as receptors for saccharide recognition in water/acetonitrile (1:1) and in DMSO. Porphyrin and metalloporphyrin macrocycles with two to four 1,1'-binaphthyl substituents and multiple hydroxy groups generate a binding site for saccharides that incorporates hydrogen-bonding hydroxy groups together with the aromatic hydrophobic pocket. The specificity for di- and trisaccharides is governed by the cavity size. The mechanism of binding has been studied by 1H NMR spectroscopy and the role of H-bonding and CH-pi interactions has been evaluated; the ability to bind saccharides has been demonstrated by the surface plasmon resonance (SPR) technique. The application of these macrocyclic receptors to sensor development is also presented.
Rusin
Oleksandr
O
Institute of Chemical Technology, Department of Analytical Chemistry, Prague, Czech Republic.
Lang
Kamil
K
Král
Vladimír
V
D015374:Biosensing Techniques / Q000379:methods*; D050260:Carbohydrate Metabolism; D002241:Carbohydrates / Q000032:analysis*; D002352:Carrier Proteins; D007501:Iron / Q000737:chemistry; D008665:Metalloporphyrins / Q000737:chemistry; D018716:Molecular Mimicry; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000737:chemistry* / Q000378:metabolism; D011166:Porphyrins / Q000737:chemistry* / Q000378:metabolism; D011956:Receptors, Cell Surface; D012995:Solubility; D020349:Surface Plasmon Resonance
D002241:Carbohydrates; D002352:Carrier Proteins; D008665:Metalloporphyrins; D011084:Polycyclic Aromatic Hydrocarbons; D011166:Porphyrins; D011956:Receptors, Cell Surface; C055213:saccharide-binding proteins; D007501:Iron