3 years ago

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

Sequence-Specific β-Peptide Synthesis by a Rotaxane-Based Molecular Machine
Malcolm A. Y. Gall, John W. Ward, David A. Leigh, Daniel J. Tetlow, Sonja Kuschel, Matthew O. Kitching, Guillaume De Bo
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.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b05850

DOI: 10.1021/jacs.7b05850

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