1:00 PM - *SM12.03.01
Metal-Binding Peptoids as a New Platform for the Development of Functional Bio-Inspired Materials and Supramolecular Peptoid Architectures
Technion–Israel Institute of Technology1
Peptoids, N-substituted glycine oligomers, are an important class of peptide mimics that are generated from primary amines rather than from amino acids. Their facile and efficient synthesis on solid phase support enables the incorporation of various functional groups at specified N-positions along their spine including metal-binding ligands and catalysts.1 Peptoids can adopt polyproline type helices if the majority of their sequence consists of chiral bulky pendent groups.2 Such side-chains are structure inducers but they have no functional value. In my talk I will present the inclusion of metal-binding ligands within peptoid sequences as a new platform for the development of functional bio-inspired materials and supramolecular peptoid architectures. Thus, I will describe: (i) Controlled aggregation of Ag(0) NPs at room temperature in water near neutral pH mediated by peptoids, where tuning the sequence or of the peptoid or changing the metal-binding ligand impact the morphology of the Ag(0) NPs assemblies.3 (ii) Cu(II) mediated self-assembly of short peptoids to form double-stranded peptoid helicates,4 and distinct copper-peptoid duplexes, where changing only one non-coordinating side-chain leads to different supramolecular structures including tightly packed helical rods or nano-channels, and to different the pore sizes of the nano-channels.5 The selective recognition abilities of the nano-channels towards biologically relevant small molecules and anions will be also demonstrated. (iii) The direct correlation between the structure of short metal-binding peptoids varied in their monomer sequence, and the photoluminescence of their Ru(II) complexes, where .helical peptoids do not affect the fluorescence of the embedded Ru(II) chromophore, while unstructured peptoids lead to its significant decay.6
1. (a) T. Zabrodski, M. Baskin, P. Jeya Kaniraj, G. Maayan Synlett 2015, A1. (b) P. Jeya Kaniraj, G. Maayan, Chem. Commun. 2015, 11096. (c) M. Baskin, G. Maayan, Chem. Sci. 2016, 7, 2809.
2. (a) K. Kirshenbaum et al., Proc. Natl. Acad. Sci., USA 1998, 95, 4303. (b) B.C. Gorske, et al. J. Am. Chem. Soc., 2007, 129, 8928. (c) O. Royet, et al., J. Am. Chem. Soc. 2017, 139, 13533
3. (a) H. Tigger-Zaborov, G. Maayan, J. Coll. Inter. Sci. 2017, 508, 56-64. (b) H. Tigger-Zaborov, G. Maayan J. Coll. Inter. Sci. 2019, 533, 598-603.
4. T. Ghosh, N. Fridman, M. Kosa, G. Maayan, Angew. Chem. Int. Ed. 2018, 57, 7703.
5. P. Ghosh, N. Fridman, G. Maayan, Chem – A Eur. J, in press.
6. L. Zborovsky, H. Tigger-Zaborov, G. Maayan, Chem. Eur. J. 2019, 25, 9098 –9107.