Selective Encapsulation of Disaccharide Xylobiose by an Aromatic Foldamer Helical Capsule

Saha, Subrata; Kauffmann, Brice; Ferrand, Yann und Huc, Ivan (2018): Selective Encapsulation of Disaccharide Xylobiose by an Aromatic Foldamer Helical Capsule. In: Angewandte Chemie-International Edition, Vol. 57, No. 41: pp. 13542-13546

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 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.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Pharmacy
• Subjects: 500 Science > 540 Chemistry
• ISSN: 1433-7851
• Language: English