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1,1′‐Binaphthyl‐Substituted Macrocycles as Receptors for Saccharide Recognition
Author(s) -
Rusin Oleksandr,
Lang Kamil,
Král Vladimír
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020201)8:3<655::aid-chem655>3.0.co;2-d
Subject(s) - chemistry , surface plasmon resonance , receptor , hydrogen bond , molecular recognition , acetonitrile , stereochemistry , porphyrin , proton nmr , combinatorial chemistry , molecule , organic chemistry , biochemistry , nanotechnology , materials science , nanoparticle
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 1 H NMR spectroscopy and the role of H‐bonding and CH–π 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.