科学杂志 人工合成糖类分子受体
[b]SCIENCE VOL 318 26 OCTOBER 2007 619A Synthetic Lectin Analog for Biomimetic Disaccharide Recognition[/b]
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 (b-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.
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