Publication Date:
2007-10-27
Description:
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.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Ferrand, Yann -- Crump, Matthew P -- Davis, Anthony P -- New York, N.Y. -- Science. 2007 Oct 26;318(5850):619-22.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/17962557" target="_blank"〉PubMed〈/a〉
Keywords:
*Biomimetics
;
Calorimetry
;
Cellobiose/chemistry
;
Circular Dichroism
;
Disaccharides/*chemistry
;
Hydrogen Bonding
;
Lectins/*chemical synthesis/*chemistry
;
Magnetic Resonance Spectroscopy
;
Molecular Conformation
;
Molecular Structure
;
Monosaccharides/chemistry
;
Protons
;
Spectrometry, Fluorescence
;
Thermodynamics
Print ISSN:
0036-8075
Electronic ISSN:
1095-9203
Topics:
Biology
,
Chemistry and Pharmacology
,
Computer Science
,
Medicine
,
Natural Sciences in General
,
Physics
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