Sequence-Specific β-Peptide Synthesis by a Rotaxane-Based Molecular Machine

De Bo, Guillaume; Gall, Malcolm A.Y.; Kitching, Matthew O.; Kuschel, Sonja; Leigh, David A.; Tetlow, Daniel J.; Ward, John W.

doi:10.1021/jacs.7b05850

Sequence-Specific β-Peptide Synthesis by a Rotaxane-Based Molecular Machine

De Bo, Guillaume; Gall, Malcolm A.Y.; Kitching, Matthew O.; Kuschel, Sonja; Leigh, David A.; Tetlow, Daniel J.; Ward, John W.

Authors

Guillaume De Bo

Malcolm A.Y. Gall

Dr Matthew Kitching matthew.o.kitching@durham.ac.uk
Royal Society University Research Fellow

Sonja Kuschel

David A. Leigh

Daniel J. Tetlow

John W. Ward

Abstract

We report on the synthesis and operation of a three-barrier, rotaxane-based, artificial molecular machine capable of sequence-specific β-homo (β3) peptide synthesis. The machine utilizes nonproteinogenic β3-amino acids, a class of amino acids not generally accepted by the ribosome, particularly consecutively. Successful operation of the machine via native chemical ligation (NCL) demonstrates that even challenging 15- and 19-membered ligation transition states are suitable for information translation using this artificial molecular machine. The peptide-bond-forming catalyst region can be removed from the transcribed peptide by peptidases, artificial and biomachines working in concert to generate a product that cannot be made by either machine alone.

Citation

De Bo, G., Gall, M. A., Kitching, M. O., Kuschel, S., Leigh, D. A., Tetlow, D. J., & Ward, J. W. (2017). Sequence-Specific β-Peptide Synthesis by a Rotaxane-Based Molecular Machine. Journal of the American Chemical Society, 139(31), 10875-10879. https://doi.org/10.1021/jacs.7b05850

Journal Article Type	Article
Online Publication Date	Jul 26, 2017
Publication Date	Aug 9, 2017
Deposit Date	Sep 18, 2017
Publicly Available Date	Jul 19, 2018
Journal	Journal of the American Chemical Society
Print ISSN	0002-7863
Electronic ISSN	1520-5126
Publisher	American Chemical Society
Peer Reviewed	Peer Reviewed
Volume	139
Issue	31
Pages	10875-10879
DOI	https://doi.org/10.1021/jacs.7b05850

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Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of the American Chemical Society, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jacs.7b05850.