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A Synthetic Lectin Analog for Biomimetic Disaccharide Recognition
Abstract
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 (β-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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Cited by
Aromatic Rings in Chemical and Biological Recognition: Energetics and Structures
Salonen, L. M., Ellermann, M., & Diederich, F. (2011) · Angewandte Chemie International Edition · doi:10.1002/anie.201007560 · Cited by 1,539
Beuerle, F., & Gole, B. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201710190 · Cited by 528
Glucose Sensing in Supramolecular Chemistry
Sun, X., & James, T. D. (2015) · Chemical Reviews · doi:10.1021/cr500562m · Cited by 386
Solís, D., Bovin, N. V., Davis, A. P., Jiménez-Barbero, J., Romero, A., Roy, R., Smetana, K., & Gabius, H.-J. (2015) · Biochimica et Biophysica Acta (BBA) - General Subjects · doi:10.1016/j.bbagen.2014.03.016 · Cited by 222
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Metadata
- Authors
- Ferrand, Y., Crump, M. P., & Davis, A. P.
- Venue
- Science
- Published
- 2007-10-26
- Volume
- 318
- Issue
- 5850
- Pages
- 619-622
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2157740440
- Cited by
- 325
- References
- 0
- FWCI
- 14.12
- Type
- journal article
- Language
- en
- Open access
- closed
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