Naphthalene dioxygenases

Sulfoxidations are not restricted to MOs but can also be carried out by dioxygenases. For example. Pseudomonas mutant strain UV4 producing a toluene dioxygenase (TOO) and Pseudomonas NCIMB 8859 expressing a naphthalene dioxygenase (NDO) were used to oxidize aryl sulfides to antipodal chiral sulfoxides [203]. 

Figure 10.36 Enzyme-catalyzed asymmetric synthesis of a pancratistatin analog using a naphthalene dioxygenase and RhuA-catalyzed aldolization for the creation of four contiguous stereocenters.

Fig. 2. Ribbon diagram of the structures of (a) the water-soluble Rieske fragment from bovine heart bci complex (ISF, left, PDB file IRIE), (b) the water-soluble Rieske fragment from spinach b f complex (RFS, middle, PDB file IRFS), and (c) the Rieske domain of naphthalene dioxygenase (NDO, right, PDB file INDO). The [2Fe-2S] cluster is shown in a space-filling representation, the ligands as ball-and-stick models, and residues Pro 175 (ISF)/Pro 142 (RFS)/Pro 118 (NDO) as well as the disulfide bridge in the ISF and RFS as wireframes.

Protein cytochrome hci complex cytochrome 6e/complex naphthalene dioxygenase... 

An iron sulfur-flavoprotein that transfers electrons to the ferredoxin, as in naphthalene dioxygenase (class III)... 

Naphthalene dioxygenase from P. putida strain FI is able to oxidize a number of haloge-nated ethenes, propenes, and butenes, and d5 -hept-2-ene and cis-oct-2-ene (Lange and Wackett 1997). Alkenes with halogen and methyl substituents at double bonds form allyl alcohols, whereas those with only alkyl or chloromethyl groups form diols. 

Gibson DT, Resnick SM, Lee K, Brand JM, Torok DS, Wackett LP, Schocken MJ, Haigler BE (1995) Desaturation, dioxygenation, and monooxygenation reactions catalysed by naphthalene dioxygenase from Pseudomonas sp. strain 9S16-4. J Bacteriol 111 2615-2621. 

Lee K, DT Gibson DT (1996) Toluene and ethylbenzene oxidation by purified naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4. Environ Microbiol 62 3101-3106. 

Suen W-C, BE Haigler, JC Spain (1996) 2,4-dinitrotoluene dioxygenase from Burkholderia sp strain DNT similarity to naphthalene dioxygenase. J Bacteriol 178 4926-4934. 

Zhou N-Y, J Al-Dulayymi, MS Baird, PA Williams (2002) Salicylate 5-hydroxylase from Ralstonia sp. strain U2 a monooxygenase with close relationships to and shared electron transport proteins with naphthalene dioxygenase. / Bacfen o/ 184 1547-1555. 

Herrick JB, KG Stuart-Keil, WC Ghiorse, EL Madsen (1997) Natural horizontal transfer of a naphthalene dioxygenase gene between bacteria native to a coal tar-contaminated field site. Appl Environ Microbiol 63 2330-2337. 

Details of the mechanism of naphthalene dioxygenase during a single turnover of the enzyme have been revealed, and conhrmed the separate roles of the dioxygenase and the ferredoxin electron transfer protein. This made it possible to propose a reaction cycle for the reaction (Wolfe et al. 2001). 

Ensley BD, DT Gibson (1983) Naphthalene dioxygenase purification and properties of a terminal oxygenase component. J Bacteriol 155 505-511. 

Haigler BE, DT Gibson (1990a) Purification and properties of ferredoxiupjj p, a component of naphthalene dioxygenase from Pseudomonas sp. strain NC1B9816. J Bacteriol 172 465-468. 

Larkin MJ, CCR Allen, LA Kulakov, DA Lipscomb (1999) Purification and characterization of a novel naphthalene dioxygenase irom Rhodococcus sp. strain NCIMB 12038. J Bacterial 181 6200-6204. 

Resnick SM, DT Gibson (1996) Regio- and stereospecific oxidation of fluorene, dibenzofuran, and dibenzothiophene by naphthalene dioxygenase from Pseudomonas sp. strain NCIB-4. Appl Environ Microbiol 62 4073-4080. 

Simon Ml, TD Osslund, R Saunders, BD Ensley, S Suggs, A Harcourt, W-C Suen, DL Cruden, DT Gibson, GJ Zylstra (1993) Sequences of genes encoding naphthalene dioxygenase in Pseudomonas putida strains G7 and NCIB 9816-4. Gene 127 31-37. 

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