Bacterial dioxygenases

FIGURE 3.2 Classification of bacterial dioxygenases. (From Neilson, A.H. and Allard, A.-S. Microbial metabolism of PAHs and heteroarenes. The Handbook of Environmental Chemistry, Vol. 3J, pp. 1-80, Springer, 1998. With permission.)... 

The main classes of bacterial dioxygenases have already been outlined in Figure 3.1. 

Mason, J.R. and R. Cammack. 1992. The electron-transport proteins of hydroxylation bacterial dioxygenases. Annu. Rev. Microbiol. 46 277-305. 

Benzene c -diols, namely, cw-3,5-cyclohexadien-l,2-diols abbreviated as DHCD, can be used for synthesis of poly(para-phenylene) (PPP), which is a material with high thermal stability and electricity conducting ability when doped. Several types of bacterial dioxygenases, that can catalyze the conversion of aromatic componnds to their corresponding c -diols, which can be polymerized to form PPP, are discnssed. 

A number of instances can be cited from the literature wherein the isosteres had similar transformations. Bacterial dioxygenase-catalyzed ci5-dihydroxylation of the tetracyclic arene benzo[c]phenanthrene was found to occur exclusively at fjord region (cavity region) bonds. The isosteric compounds benzo[b]naphthol [l,2-d]furan and benzo[b]naphthol[l,2-d]thiophene were also similarly ci5-dihydroxylated at the fjord region bonds by bacterial dioxygenases (Boyd et al., 2001) (see Fig. 4.3). The isosteres 1,2-dihydronaphthalene, 2,3-dihydrobenzothiophene, and 2,3-dihydro-benzofuran gave similar corresponding diol products on incubation with Pseudomonas putida UV4. Microbes that possess the metabolic pathways to metabolize benzene, when substituted by... 

---