Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 41, Pages 13542-13546Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201808370
Keywords
carbohydrates; disaccharides; foldamers; helical capsules; molecular recognition
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Funding
- European Research Council under the European Union's Seventh Framework Programme [ERC-2012-AdG-320892]
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Xylobiose sequestration in a helical aromatic oligoamide capsule was evidenced by circular dichroism, NMR spectroscopy, and crystallography. The preparation of the 5 kDa oligoamide sequence was made possible by the transient use of acid-labile dimethoxybenzyl tertiary amide substituents that disrupt helical folding and prevent double helix formation. Binding of other disaccharides was not detected. Crystallographic data revealed a complex composed of a D-xylobiose anomer and two water molecules accommodated in the right-handed helix. The disaccharide was found to adopt an unusual all-axial compact conformation. A dense network of 18 hydrogen bonds forms between the guest, the cavity wall, and the two water molecules.
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