Selective Encapsulation of Disaccharide Xylobiose by an Aromatic Foldamer Helical Capsule

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.