Direct biocatalytic synthesis of functionalized catechols: a green alternative to traditional methods with high effective mass yield

Abstract

Several catechols have been prepared directly from aromatic precursors by treatment with the recombinant organism Escherichia coli JM109 (pDTG602), which expresses both toluene dioxygenase (TDO) and dihydrocatechol dehydrogenase (DHCD), the first two enzymes in the natural biodegradation pathway of aromatics by Pseudomonas species. The yields and the ease of preparation of these compounds are compared with traditional chemical methods. For three of the products, the E value and EMY (effective mass yield, is defined as the percentage of the mass of desired product relative to the mass of all non-benign materials in its synthesis, see ref. 9) are calculated and compared with those obtained by traditional methods to indicate the green component of the preparation. Potential for direct introduction of the catechol unit to various natural product synthons is discussed.