A Synthetic Lectin Analog for Biomimetic Disaccharide Recognition
Yann Ferrand,
Matthew P. Crump,
Anthony P. Davis*
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 (ß-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.
* To whom correspondence should be addressed. E-mail: anthony.davis{at}bristol.ac.uk
