A rotaxane-based molecular machine capable of performing sequence specific synthesis of a tripeptide was recently reported by our group. This small molecular machine mimics the operation of ribosomal peptide synthesis in that it creates a defined sequence from a molecular template. The ring carries a thiolate group that iteratively removes proteinogenic amino acids from the strand and transfers them to a peptide elongation site through native chemical ligation (NCL).This first generation peptide synthesiser is an amazing molecular machine, but still only a very primitive analogue of the ribosome, which not only operates faster, but also synthesises much longer polypeptide chains.Here we report the successful preparation, using a rotaxane elongation strategy, of artificial molecular machines operating on oligomeric and polymeric tracks allowing new insights into the limitations of the NCL mechanism. The operation of a molecular machine containing multiple building blocks on a polymeric track represents an enormous advancement in the field, since most of the molecular machines and devices reported to date have been operated only on shorter model systems.

Towards man-made ribosomes: Peptide synthesis by an artificial small-molecule machine on a polymeric track

248th National Meeting (2014)

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