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Synthetic polymers - manufacture to order

Protein synthesis in the cell is a very complex procedure. Scientists have mimicked the transcription process and manufactured a molecule that is actually found in naturally occurring peptides such as bacterial toxins.
Synthetic polymers - manufacture to order
Transcription in a real live cell uses a template, messenger RNA (mRNA) to code for the protein and assemble the amino acid building blocks in the cell ribosome. The EU-funded MOLFACTORY (Towards a ‘molecular factory’: Processive sequence-selective synthesis with a synthetic molecular machine) project has constructed a synthetic molecular machine using [2]rotaxane.

Rotaxane is a dumbbell-shaped molecule that is threaded through a ring-shaped structure called a macrocycle. The ends of the dumbbell are often larger than the internal diameter of the ring preventing unthreading and keeping this unusual shape intact.

In the MOLFACTORY machinery, the macrocycle acts as both a catalyst and a molecular transporter. Essentially, it removes bulky aromatic amino acid substituents from a sequence-specific thread and carries them in turn to the next amino acid before catalysing the formation of the amide bond between them.

The artificial molecular machine therefore ensures the monomers are assembled in the right order. A dye molecule is tethered to the end of the track, which changes fluorescence intensity when each unit has been added and a bond is formed. Further work is anticipated to achieve this.

The team optimised the synthetic route and determined the chemical structure of the backbone of the machine. Alkyne and azide functionalised tyrosine barriers (each having different amino acids) were synthesised. Reactions successfully performed include amide coupling and sequential copper-catalysed Huisgen cycloaddition.

The active metal template method was used to construct the rotaxane with different amino ester barriers and the products were characterised with nuclear magnetic resonance spectroscopy. Machine activation and operation was achieved by removal of the protecting groups.

MOLFACTORY has taken the development of synthetic molecular machines far beyond the state-of-the-art. Building on their work will mean machines that can synthesise oligomers and polymers to order. Use in industry is wide and includes plasticisers, biomedical products and manufacture of genetic tools for research and pharmaceutical use.

Related information

Keywords

Synthetic polymer, manufacture, rotaxane, catalyst, amide
Record Number: 180906 / Last updated on: 2016-03-24
Domain: Biology, Medicine
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