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

by Lewandowski, Bartosz , Aldegunde, María J. , Gramlich, Philipp M. E. , Leigh, David A. , Kuschel, Sonja , Heckmann, Dominik , Fernandes, Antony E. , De Bo, Guillaume , D'Souza, Daniel M. , Ward, John W. , Goldup, Stephen M. , Papmeyer, Marcus

in Amino Acid Sequence / Amino acids / Assembling / Biosynthesis / Bonding / Chemical Phenomena / Chemicals / Chemistry Techniques, Synthetic / Crystals / Ions / Layoffs / Ligation / Mass spectrometry / Mass spectroscopy / Materials / messenger RNA / Molecular biology / Molecular Structure / nitrogen / Nuclear Magnetic Resonance, Biomolecular / Peptides / Peptides - chemical synthesis / Peptides - chemistry / proteins / Residential buildings / Ribonucleic acid / ribosomes / RNA / Rotaxanes / Rotaxanes - chemistry / Tandem Mass Spectrometry / Terminals / Thiols / Threaded

2013

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2013

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2013

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Journal Article

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

Lewandowski, Bartosz,

Aldegunde, María J.,

Gramlich, Philipp M. E.,

Leigh, David A.,

Kuschel, Sonja,

Heckmann, Dominik,

Fernandes, Antony E.,

De Bo, Guillaume,

D'Souza, Daniel M.,

Ward, John W.,

Goldup, Stephen M.,

Papmeyer, Marcus

2013

Overview

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 ∼10 18 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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Publisher

American Association for the Advancement of Science,The American Association for the Advancement of Science

Subject

/ Bonding