A synthetic lectin analog for biomimetic disaccharide recognition.
Carbohydrate recognition is biologically important but intrinsically challenging, for both nature and host-guest chemists. Saccharides are complex, subtly variable, and camouflaged by hydroxyl groups that hinder discrimination between substrate and water. We have developed a rational strategy for the biomimetic recognition of carbohydrates with all-equatorial stereochemistry (beta-glucose, analogs, and homologs) and have now applied it to disaccharides such as cellobiose. Our synthetic receptor showed good affinities, not unlike those of some lectins (carbohydrate-binding proteins). Binding was demonstrated by nuclear magnetic resonance, induced circular dichroism, fluorescence spectroscopy, and calorimetry, all methods giving self-consistent results. Selectivity for the target substrates was exceptional; minor changes to disaccharide structure (for instance, cellobiose to lactose) caused almost complete suppression of complex formation.
Ferrand
Yann
Y
School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
Crump
Matthew P
MP
Davis
Anthony P
AP
D032701:Biomimetics; D002151:Calorimetry; D002475:Cellobiose / Q000737:chemistry; D002942:Circular Dichroism; D004187:Disaccharides / Q000737:chemistry*; D006860:Hydrogen Bonding; D037102:Lectins / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry; D011522:Protons; D013050:Spectrometry, Fluorescence; D013816:Thermodynamics
D004187:Disaccharides; D037102:Lectins; D009005:Monosaccharides; D011522:Protons; C524153:disaccharide receptor; D002475:Cellobiose