A research group led by Professor Yoshito Watanabe of Nagoya University has developed a chemical substance that can turn the enzyme switch in Escherichia coli into an "ON state", and benzene is used under mild conditions at room temperature and normal pressure. We have succeeded in developing a bacterium that converts to phenol.

 Benzene is a stable hydrocarbon with the simplest structure, and the "cumene method" is the main industrial method for converting benzene into phenol, which is a raw material for pharmaceuticals and dyes.However, the reaction by this method needs to be carried out at high temperature and high pressure, and a large amount of acetone, which is an unnecessary by-product, is produced. Therefore, the development of a new phenol synthesis method using benzene as a starting material has been required.

 This time, the research group biosynthesizes an oxidase called "cytochrome P450BM3" in Escherichia coli, and when a newly developed chemical substance (pseudo substrate [Note]) incorporated into Escherichia coli is added to the reaction solution, benzene is converted to phenol. It was revealed that it would be done.In this method, benzene can be converted to phenol under mild conditions of normal temperature and pressure.In addition, the yield of phenol (ratio of benzene converted to phenol) is as high as 5% in the reaction for 59 hours.In addition, by adjusting the reaction time, hydroquinone in which phenol is further oxidized can be produced.

 Since the intracellular reaction system developed this time can directly and selectively convert benzene to phenol under mild conditions at normal temperature and pressure, it can be expected to be applied as a new method for synthesizing phenol.Further, by using a pseudo substrate that activates the enzyme, the naturally occurring enzyme can be used as it is, so that it is not necessary to modify the enzyme itself by genetic manipulation.Furthermore, we have developed a completely new concept reaction system that enables hydroxylation of benzene simply by adding a pseudo-substrate to the culture medium of cells.

Note: A dummy substance whose structure is very similar to the compound targeted by the enzyme.Also called a decoy molecule.

Paper information:[Angewandte Chemie International Edition] Whole-Cell Biotransformation of Benzene to Phenol Catalysed by Intracellular Cytochrome P450BM3 Activated by External Additives

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