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Biomimetic and bioinspired molecular electrets. How to make them and why does the established peptide chemistry not always work?

Skonieczny, Kamil and Espinoza, Eli M. and Derr, James B. and Morales, Maryann and Clinton, Jillian M. and Xia, Bing and Vullev, Valentine I. (2020) Biomimetic and bioinspired molecular electrets. How to make them and why does the established peptide chemistry not always work? Pure and Applied Chemistry, 92 (2). pp. 275-299. ISSN 1365-3075. doi:10.1515/pac-2019-0111.

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“Biomimetic” and “bioinspired” define different aspects of the impacts that biology exerts on science and engineering. Biomimicking improves the understanding of how living systems work, and builds tools for bioinspired endeavors. Biological inspiration takes ideas from biology and implements them in unorthodox manners, exceeding what nature offers. Molecular electrets, i.e. systems with ordered electric dipoles, are key for advancing charge-transfer (CT) science and engineering. Protein helices and their biomimetic analogues, based on synthetic polypeptides, are the best-known molecular electrets. The inability of native polypeptide backbones to efficiently mediate long-range CT, however, limits their utility. Bioinspired molecular electrets based on anthranilamides can overcome the limitations of their biological and biomimetic counterparts. Polypeptide helices are easy to synthesize using established automated protocols. These protocols, however, fail to produce even short anthranilamide oligomers. For making anthranilamides, the residues are introduced as their nitrobenzoic-acid derivatives, and the oligomers are built from their C- to their N-termini via amide-coupling and nitro-reduction steps. The stringent requirements for these reduction and coupling steps pose non-trivial challenges, such as high selectivity, quantitative yields, and fast completion under mild conditions. Addressing these challenges will provide access to bioinspired molecular electrets essential for organic electronics and energy conversion.

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Additional Information:© 2020 IUPAC & De Gruyter. This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. For more information, please visit: Published Online: 2019-08-10; Published in Print: 2020-02-25. A collection of invited papers based on presentations at the 4th International Conference on Bioinspired and Biobased Chemistry & Materials (NICE-2018), Nice, France, 14–17 October 2018. Funding for this work was from the USA National Science Foundation, Funder Id:, grants CHE 1465284 and CHE 1800602.
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Subject Keywords:bioinspired; biomimetic; electrets; NICE-2018; peptide synthesis; selective reduction
Issue or Number:2
Record Number:CaltechAUTHORS:20200319-104518736
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Official Citation:Skonieczny, K., Espinoza, E., Derr, J., et al. (2019). Biomimetic and bioinspired molecular electrets. How to make them and why does the established peptide chemistry not always work?. Pure and Applied Chemistry, 92(2), pp. 275-299. Retrieved 19 Mar. 2020, from doi:10.1515/pac-2019-0111
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:101996
Deposited By: Tony Diaz
Deposited On:19 Mar 2020 17:57
Last Modified:16 Nov 2021 18:07

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