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Selective Encapsulation of Disaccharide Xylobiose by an Aromatic Foldamer Helical Capsule
Language
EN
Article de revue
This item was published in
Angewandte Chemie (International ed. in English). 2018, vol. 57, n° 41, p. 13542-13546
English Abstract
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 ...Read more >
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 alpha 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.Read less <
English Keywords
carbohydrates
disaccharides
foldamers
helical capsules
molecular recognition