Homochiral versus Heterochiral Dimeric Helical Foldamer Bundles: Chlorinated‐Solvent‐Dependent Self‐Sorting

Menke, Friedericke S.; Wicher, Barbara ; Maurizot, Victor and Huc, Ivan (2023): Homochiral versus Heterochiral Dimeric Helical Foldamer Bundles: Chlorinated‐Solvent‐Dependent Self‐Sorting. In: Angewandte Chemie International Edition, Vol. 62, No. 12

Abstract

Aromatic oligoamide sequences programmed to fold into stable helical conformations were designed to display a linear array of hydrogen-bond donors and acceptors at their surface. Sequences were prepared by solid-phase synthesis. Solution 1H NMR spectroscopic studies and solid-state crystallographic structures demonstrated the formation of stable hydrogen-bond-mediated dimeric helix bundles that could be either heterochiral (with a P and an M helix) or homochiral (with two P or two M helices). Formation of the hetero- or homochiral dimers could be driven quantitatively using different chlorinated solvents—exemplifying a remarkable case of either social or narcissistic chiral self-sorting or upon imposing absolute handedness to the helices to forbid PM species.

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