The whole-cell fermentation of aromatic coumpounds with Escherichia coli JM109 (pDTG601) on a medium scale (10−15 L) produces enantiopure cyclohexadienediols. A detailed procedure for the fermentation is described, and yields for several metabolites are provided. A similar procedure using E. coli JM109 (pDTG602) affords catechols. The dienediols are useful for asymmetric synthesis, and several important targets originating from these metabolites are tabulated.

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.

A series of substituted arenes containing remote chiral centers were screened as substrates for toluene dioxygenase (TDO). The absolute stereochemistry of the new metabolites was determined by chemical and spectroscopic correlation with synthetic standards. There was no evidence for kinetic resolution ; enantiomers were indiscriminately processed by the enzyme to diastereomeric pairs, which were separable upon derivatization. Some of these new metabolites are useful as synthons for morphine synthesis. Full experimental details are reported for those new compounds stable to isolation and for derivatives of those that are unstable.

While rare in pediatrics, intraperitoneal neoplasms occur in children, and CT is useful in identifying these peritoneal neoplasms.

Cyclopropylbenzene was subjected to whole-cell fermentation with either Escherichia coli JM109 (pDTG601) or E. coli JM109 (pDTG602), expressing toluene dioxygenase and toluene dioxygenase – dihydrodiol dehydrogenase enzymes, respectively. The corresponding metabolites, 3-cyclopropylcyclohexa-3,5-diene-1,2-diol (3) and 3-cyclopropylbenzene-1,2-diol (5) have been isolated in yields of 2.5 and 1 g L–1, respectively. The absolute stereochemistry correlation for 3 is provided, along with a preliminary discussion of its potential in asymmetric synthesis. Possible mechanistic implications are indicated for the enzymatic oxygenation through the use of calculations. Experimental data are provided for all new compounds.Key words: cyclopropylbenzene, bio-oxidation, cis-diene diol, catechol, JM109 (pDTG601), JM109 (pDTG602), dioxygenase.