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1,1′-Binaphthyl-Substituted Macrocycles as Receptors for Saccharide Recognition by Oleksandr Rusin; Kamil Lang; Vladimír Král is a Chemistry article available to read on EtoBox.

What is 1,1′-Binaphthyl-Substituted Macrocycles as Receptors for Saccharide Recognition about?

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.

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Author

Oleksandr Rusin; Kamil Lang; Vladimír Král

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 0947-6539)

Published

2002

Language

EN

Field

Chemistry (Physical Sciences)