Title

Selective Encapsulation of Disaccharide Xylobiose by an Aromatic Foldamer Helical Capsule.

Authors

Saha, Subrata; Kauffmann, Brice; Ferrand, Yann; Huc, Ivan

Abstract

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 α 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.

Subjects

ENCAPSULATION (Catalysis); DISACCHARIDES; NUCLEAR magnetic resonance spectroscopy; CRYSTALLOGRAPHY; DATA analysis

Publication

Angewandte Chemie, 2018, Vol 130, Issue 41, p13730

ISSN

0044-8249

Publication type

Academic Journal

DOI

10.1002/ange.201808370