title: Mechanochemical Encapsulation of Fullerenes in Peptidic Containers Prepared by Dynamic Chiral Self-Sorting and Self-Assembly.
abstract: Molecular capsules composed of amino acid or peptide derivatives connected to resorcin[4]arene scaffolds through acylhydrazone linkers have been synthesized using dynamic covalent chemistry (DCC) and hydrogen-bond-based self-assembly. The dynamic character of the linkers and the preference of the peptides towards self-assembly into β-barrel-type motifs lead to the spontaneous amplification of formation of homochiral capsules from mixtures of different substrates. The capsules have cavities of around 800 Å(3) and exhibit good kinetic stability. Although they retain their dynamic character, which allows processes such as chiral self-sorting and chiral self-assembly to operate with high fidelity, guest complexation is hindered in solution. However, the quantitative complexation of even very large guests, such as fullerene C60 or C70 , is possible through the utilization of reversible covalent bonds or the application of mechanochemical methods. The NMR spectra show the influence of the chiral environment on the symmetry of the fullerene molecules, which results in the differentiation of diastereotopic carbon atoms for C70 , and the X-ray structures provide unique information on the modes of peptide-fullerene interactions.
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
authors.forename: Marek
authors.initials: M
authors.lastname: Szymański
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
authors.forename: Michał
authors.initials: M
authors.lastname: Wierzbicki
authors.affiliation: Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, 61-614, Poznan, Poland.|Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704, Poznan, Poland.
authors.forename: Mirosław
authors.initials: M
authors.lastname: Gilski
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
authors.forename: Hanna
authors.initials: H
authors.lastname: Jędrzejewska
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
authors.forename: Marcin
authors.initials: M
authors.lastname: Sztylko
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
authors.forename: Piotr
authors.initials: P
authors.lastname: Cmoch
authors.affiliation: Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland.
authors.forename: Aleksander
authors.initials: A
authors.lastname: Shkurenko
authors.affiliation: Faculty of Chemistry, A. Mickiewicz University, Umultowska 89b, 61-614, Poznan, Poland. mariuszj@amu.edu.pl.|Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704, Poznan, Poland. mariuszj@amu.edu.pl.
authors.forename: Mariusz
authors.initials: M
authors.lastname: Jaskólski
authors.affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland. agnieszka.szumna@icho.edu.pl.
authors.forename: Agnieszka
authors.identifier: http://orcid.org/0000-0003-3869-1321
authors.initials: A
authors.lastname: Szumna
mesh_terms: D047250:Calixarenes / Q000737:chemistry*; D037741:Fullerenes / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010455:Peptides / Q000737:chemistry*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D037741:Fullerenes; D010455:Peptides; C466160:resorcinarene; D047250:Calixarenes; D010649:Phenylalanine; C069837:fullerene C60
keywords: chirality; fullerenes; mechanochemistry; peptide mimics; supramolecular chemistry