Promoting helicity in carbohydrate-containing foldamers through long-range hydrogen bonds

A sensor system to probe the propensity of carbohydrates to induce helical structures through long-range hydrogen bonds, based on a C(2)-symmetric xylylene bis(thiourea) arrangement, is reported; the formation of intermolecular complexes with benzoate anion promotes helix uncoiling, the free energy...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2007-01 (8), p.831-833
Main Authors: Rodríguez-Lucena, David, Benito, Juan M, Mellet, Carmen Ortiz, García Fernández, José M
Format: Article
Language:English
Subjects:
Benzoates - chemistry
Carbohydrate Conformation
Carbohydrates - chemistry
Hydrogen Bonding
Indicators and Reagents
Magnetic Resonance Spectroscopy
Models, Molecular
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Summary:A sensor system to probe the propensity of carbohydrates to induce helical structures through long-range hydrogen bonds, based on a C(2)-symmetric xylylene bis(thiourea) arrangement, is reported; the formation of intermolecular complexes with benzoate anion promotes helix uncoiling, the free energy of the process being related to helix stability.
ISSN:1359-7345
1364-548X
DOI:10.1039/b614294j