Cucurbit[7]uril: A High-Affinity Host for Encapsulation of Amino Saccharides and Supramolecular Stabilization of Their -Anomers in Water
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SCOPUS
- Title
- Cucurbit[7]uril: A High-Affinity Host for Encapsulation of Amino Saccharides and Supramolecular Stabilization of Their -Anomers in Water
- Authors
- Yoonjung Jang; Ramalingam Natarajan; Young Ho Ko; Kim, K
- Date Issued
- 2014-01-20
- Publisher
- WILEY-V C H VERLAG GMBH
- Abstract
- Cucurbit[7]uril (CB[7]), an uncharged and water-soluble macrocyclic host, binds protonated amino saccharides (D-glucosamine, D-galactosamine, D-mannosamine and 6-amino-6-deoxy-D-glucose) with excellent affinity (K-a=10(3) to 10(4)M(-1)). The host-guest complexation was confirmed by NMR spectroscopy, isothermal titration calorimetry (ITC), and MALDI-TOF mass spectral analyses. NMR analyses revealed that the amino saccharides, except D-mannosamine, are bound as -anomers within the CB[7] cavity. ITC analyses reveal that CB[7] has excellent affinity for binding amino saccharides in water. The maximum affinity was observed for D-galactosamine hydrochloride (K-a=1.6x10(4)M(-1)). Such a strong affinity for any saccharide in water using a synthetic receptor is unprecedented, as is the supramolecular stabilization of an -anomer by the host.
- Keywords
- calorimetry; host-guest systems; hydrophobic effect; molecular recognition; NMR spectroscopy; SYNTHETIC LECTIN; MOLECULAR RECOGNITION; SUGARS; RECEPTORS; BINDING; AMINOGLYCOSIDES; DERIVATIVES; CHEMISTRY
- URI
- https://oasis.postech.ac.kr/handle/2014.oak/14850
- DOI
- 10.1002/ANIE.201308879
- ISSN
- 1433-7851
- Article Type
- Article
- Citation
- ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 53, no. 4, page. 1003 - 1007, 2014-01-20
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