Cucurbit[7]uril: A High-Affinity Host for Encapsulation of Amino Saccharides and Supramolecular Stabilization of Their a-Anomers in Water
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
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| Title |
Cucurbit[7]uril: A High-Affinity Host for Encapsulation of Amino Saccharides and Supramolecular Stabilization of Their a-Anomers in Water
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| Creator |
Jang, Yoonjung
Natarajan, Ramalingam Ho Ko, Young Kim, Kimoon |
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| Subject |
Chemistry
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| Description |
Cucurbit[7]uril (CB[7]), an uncharged and watersoluble
macrocyclic host, binds protonated amino saccharides
(d-glucosamine, d-galactosamine, d-mannosamine and 6-
amino-6-deoxy-d-glucose) with excellent affinity (Ka=103 to
104m�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 a-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 (Ka=1.6 � 104m�1). Such a strong affinity for any saccharide in water using a synthetic receptor is unprecedented, as is the supramolecular stabilization of an aanomer by the host.
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| Publisher |
John Wiley & Sons
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| Date |
2014
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://www.eprints.iicb.res.in/2010/1/ANGEWANDTE_CHEMIE%2DINTERNATIONAL_EDITION__V53_(_4)1003%2D1007__;2014(17).pdf
Jang, Yoonjung and Natarajan, Ramalingam and Ho Ko, Young and Kim, Kimoon (2014) Cucurbit[7]uril: A High-Affinity Host for Encapsulation of Amino Saccharides and Supramolecular Stabilization of Their a-Anomers in Water. Angewandte Chemie International Edition, 53 (4). pp. 1003-1007. ISSN 1433-7851 |
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| Relation |
http://dx.doi.org/10.1002/anie.201308879.
http://www.eprints.iicb.res.in/2010/ |
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