Selective Dynamic Assembly of Disulfide Macrocyclic Helical Foldamers with Remote Communication of Handedness

Autor:	Nils Metzler-Nolte, Céline Douat, Makoto Takafuji, Ivan Huc, Christos Tsiamantas, Brice Kauffmann, Victor Maurizot, Hirotaka Ihara, Xavier de Hatten
Rok vydání:	2016
Předmět:	Bridging (networking) Remote communication Chemistry Stereochemistry 010405 organic chemistry Intermolecular force Disulfide bond General Chemistry General Medicine 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Intramolecular force Helix Side chain Quantitative assessment
Zdroj:	Angewandte Chemie. 128:6962-6966
ISSN:	0044-8249
DOI:	10.1002/ange.201601156
Popis:	Disulfide bridge formation was investigated in helical aromatic oligoamide foldamers. Depending on the position of thiol-bearing side chains, exclusive intramolecular or intermolecular disulfide bridging may occur. The two processes are capable of self-sorting, presumably by dynamic exchange. Quantitative assessment of helix handedness inversion rates showed that bridging stabilizes the folded structures. Intermolecular disulfide bridging serendipitously yielded a well-defined, C2 -symmetrical, two-helix bundle-like macrocyclic structure in which complete control over relative handedness, that is, helix-helix handedness communication, is mediated remotely by the disulfide bridged side chains in the absence of contacts between helices. MM calculations suggest that this phenomenon is specific to a given side chain length and requires disulfide functions.
Databáze:	OpenAIRE
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