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

Autor: Menke FS; Department of Pharmacy, Ludwig-Maximilians-University of Munich, Butenandtstr. 5-13, 81377, München, Germany., Wicher B; Department of Chemical Technology of Drugs, Poznan University of Medical Sciences, 6 Grunwaldzka St., 60-780, Poznan, Poland., Maurizot V; CBMN (UMR 5248), Univ. Bordeaux, CNRS, Bordeaux INP, 2, Rue Robert Escarpit, 33600, Pessac, France., Huc I; Department of Pharmacy, Ludwig-Maximilians-University of Munich, Butenandtstr. 5-13, 81377, München, Germany.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2023 Mar 13; Vol. 62 (12), pp. e202217325. Date of Electronic Publication: 2023 Feb 08.
DOI: 10.1002/anie.202217325
Abstrakt: 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 1 H 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.
(© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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