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.

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
• Public URL: https://durham-repository.worktribe.com/output/1348945