Oxidation of polycyclic aromatic hydrocarbons

Hammel KE, B Kalyanaraman, TK Kirk (1986) Oxidation of polycyclic aromatic hydrocarbons and dibenzo(p)dioxins by Phanerochaete chrysosporium ligninase. J Biol Chem 261 16948-16952. 

Coates JD, RT Anderson, DR Lovley (1996) Oxidation of polycyclic aromatic hydrocarbons under sulfate-reducing conditions. Appl Environ Microbiol 62 1099-1101. 

Tinoco, R., and VazquezDuhalt, R., Chemical Modification of Cytochrome C Improves Their Catalytic Properties in Oxidation of Polycyclic Aromatic Hydrocarbons. Enzyme and Microbial Technology, 1998. 22(1) pp. 8-12. 

Ortiz Leon, M. Velasco, L., and Vazquez-Duhalt, R., Biocatalytic Oxidation of Polycyclic Aromatic-Hydrocarbons by Hemoglobin and Hydrogen-Peroxide. Biochemical and Biophysical Research Communications, 1995. 215(3) pp. 968-973. 

Torres, E. Tinoco, R., and Vazquez-Duhalt, R., Biocatalytic oxidation of polycyclic aromatic hydrocarbons in media containing organic solvents. Water Science and Technology, 1997. 36(10) pp. 37 4. 

Rogoff, M. H. (1962). Chemistry of oxidation of polycyclic aromatic hydrocarbons by soil Pseudomonads, J. Bacteriol., 83, 998-1004. 

CYP1A1. In humans, of the two members, CYP1A2 is the major player while CYP1A1 is a relatively minor extrahepatic isoform associated with the oxidation of polycyclic aromatic hydrocarbons like benzo[a]pyrene. Similarly, in test rodent species it is responsible for the generation of toxic intermediates and carcinogenic metabolites (10). 

The microsomal epoxide hydrolases (microsomal EH, mEH), predominantly found in the endoplasmic reticulum, regio- and stereoselectively catalyze the hydration of both alkene and arene oxides, including oxides of polycyclic aromatic hydrocarbons. These enzymes have been purified to homogeneity from various species and tissues [22] [41 - 46], The human microsomal EH contains 455 amino acids (Mr 52.5 kDa) and is the product of the EPHX1 gene [47] (also known as HYL1 [48]). 

Cerniglia, C. E., Dodge, R. H. Gibson, D. T. (1980d). Studies on the fungal oxidation of polycyclic aromatic hydrocarbons. Botanica Marina, 23, 121-4. 

The basic structures of resins and asphaltenes are similar. Both can be formed by oxidation of polycyclic aromatic hydrocarbons. On the other hand, both can be reduced to hydrocarbons by hydrogenation, which yields moderate to large hydrocarbon molecules, hydrogen sulfide, and water. Further, resins can be converted to asphaltenes by oxidation. 

The ease of oxidation of polycyclic aromatic hydrocarbons in the gas phase481 as well as in solution is well-documented.482 195 In strong acid solutions, monopositive radical ions and/or dipositive ions, also known as oxidation dications, have been reported.271,494,495 Similar species have been observed in anodic oxidations of... 

The last entry of table 1, tetrahexylammonium benzoate, is an example of the use of molten salts as electrolytes. In this particular case, the salt is liquid at room temperature, but it has been reported that tetrabutylammonium nitrate at 150° can be used for polarographic and preparative work 7Sa-> (oxidation of polycyclic aromatic hydrocarbons). The use of molten salts as SSE s is of great interest because of the high conductivities of such media as compared to conventional SSE s and deserves further studies. 

Majcherczyk A, Johannes C, Huttermann A. Oxidation of polycyclic aromatic hydrocarbons (PAH) by laccase of Trametes versicolor. Enzyme Microb Technol 1998 22 335-341. 

Table 8.2 Oxidation of polycyclic aromatic hydrocarbon by unmodified- and pegylated and methylated cytochrome c [102]...

Harford-Cross CF, Carmichael AB, Allan FK et al (2000) Protein engineering of cytochrome P450cam (CYP101) for the oxidation of polycyclic aromatic hydrocarbons. Protein Eng 13 121-128... 

Ortiz-Leon M, Velasco L, Vazquez-Duhalt R (1995) Biocatalytic oxidation of polycyclic aromatic hydrocarbons by hemoglobin and hydrogen peroxide. Biochem Biophys Res Comm 215 968-973... 

Tinoco R, Vazquez-Duhalt R (1998) Chemical modification of cytochrome C improves their catalytic properties in oxidation of polycyclic aromatic hydrocarbons. Enzyme Microb Technol 22 8-12... 

Two comprehensive reviews of arene oxides-oxepins have been produced to date. The first review in 1967 dealt mainly with the concept of valence tautomerism in the monocyclic arene oxide-oxepin series, while the second article in 1973 also included the arene oxides of polycyclic aromatic hydrocarbons (PAH) and placed more emphasis upon their chemistry and biochemistry. In addition, a number of more speciahzed reviews dealing with aspects of arene oxide-oxepin chemistry including oxepins and hydrooxepins, solution chemistry, and roles in metabolism have appeared. The profusion of papers associated with the title arene oxides-oxepins that have appeared since 1973 (> 300 papers) allied to the significance of advances contained therein has prompted the present chapter. Particular stress is placed upon the material appearing during the period 1973-1982, with appropriate cross-references to the earlier literature. ... 

Figure 9. Structures of synthesized non-K-region arene oxides of polycyclic aromatic hydrocarbons. References to each synthesis are superscripted. See also Figure 2.

The primary goal of initial studies of the microsomal and purified epoxide-hydrolase catalyzed hydration of arene oxides of polycyclic aromatic hydrocarbons was an attempt to identify structure-activity relationships. To this end, some selected values for the hydration of a series of arene oxides are given in Table 2. One of the more obvious aspects of this study was that there is no apparent relation-... 

Penning, T. M., Ohnishi, S. T., Ohnishi, T., and Harvey, R. G. (1996). Generation of reactive oxygen species during flie enzymatic oxidation of polycyclic aromatic hydrocarbon trawi -dihydrodiols catalyzed by dihydrodiol dehydrogenase. Chem Res Toxicol 9, 84—92. 

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