Tuesday, January 15, 2013

Sequence-Specific Peptide Synthesis by an Artificial Small-Molecule Machine



Bartosz Lewandowski1,Guillaume De Bo1,John W. Ward1,Marcus Papmeyer1,Sonja Kuschel1,María J. Aldegunde2,Philipp M. E. Gramlich2,Dominik Heckmann2,Stephen M. Goldup2,Daniel M. D’Souza2,Antony E. Fernandes2,David A. Leigh1,2,*

The ribosome builds proteins by joining together amino acids in an order determined by messenger RNA. Here, we report on the design, synthesis, and operation of an artificial small-molecule machine that travels along a molecular strand, picking up amino acids that block its path, to synthesize a peptide in a sequence-specific manner. The chemical structure is based on a rotaxane, a molecular ring threaded onto a molecular axle. The ring carries a thiolate group that iteratively removes amino acids in order from the strand and transfers them to a peptide-elongation site through native chemical ligation. The synthesis is demonstrated with ~1018 molecular machines acting in parallel; this process generates milligram quantities of a peptide with a single sequence confirmed by tandem mass spectrometry. 


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