Alkene monooxygenases

Hartmans S, FJ Weber, BPM Somhorst, JAM de Bont (1991) Alkene monooxygenase from Mycobacterium E3 a multicomponent enzyme. J Gen Microbiol 137 2555-2560. 

Zhou N-Y, A Jenkins, CKN Chan, KW Chion, DJ Leak (1999) The alkene monooxygenase from Xanthobacter strain Py2 is closely related to aromatic monooxygenases and catalyzes aromatic monooxygenation of benzene, toluene, and phenol. Appl Environ Microbiol 65 1589-1595. 

Ensign SA (1996) Aliphatic and chlorinated alkenes and epoxides as inducers of alkene monooxygenase and epoxidase activities in Xanthobacter strain Py2. Appl Environ Microbiol 62 61-66. 

Small FJ, SA Ensign (1997) Alkene monooxygenase from Xanthobacter strain Py2. Purification and characterization of a four-component system central to the bacterial metabolism of aliphatic alkenes. J Biol Chem 272 24913-24920. 

The aerobic degradation of chloroethene (vinyl chloride) by Mycobacterium aurum strain LI proceeded by initial formation of an epoxide mediated by an alkene monooxygenase (Hartmans and de Bout 1992). This reaction has also been demonstrated to occur with Methylosinus trichosporium, even though subsequent reactions were purely chemical (Castro et al. 1992b). 

Prichanont, S., Leak, D.J. and Stuckey, D.C. (1998) Alkene monooxygenase-catalyzed whole cell epoxidation in a two-liquid phase system. Enzyme and Microbial Technology, 22 (6), 471 479. 

Ensign, S. A., Hyman, M. R. Arp, D. J. (1992). Cometabolic degradation of chlorinated alkenes by alkene monooxygenase in a propylene-grown Xanthobacter strain. Applied and Environmental Microbiology, 58, 3038-46. 

Chiral epoxide Alkene monooxygenase Nocardia corallina... 

In Xanthobacter sp. strain Py2 both the alkene monooxygenase and the epoxidase are induced by C2, C3, and C4 alkenes, and also by chlorinated alkenes including vinyl chloride, cis- and trans-dichlo-roethene and 1,3-dichloropropene (Ensign 1996). 

Indeed, vinyl chloride- and etiiene-grown cells of strain LI have been shown to oxidize propene to 1,2-epoxypropane [30], indicating that alkene monooxygenase was present in cells grown on both the substrates. 

NADH- and os gen-dependent alkene monooxygenase was also detected in dialyzed crude extracts of ethene- and vinyl chloride>grown cells [26]. No monooxygenase activity was detected in cells grown on acetate or succinate. 

The presence of alkene monooxygenase activity in extracts of vinyl chloride-grown M. aurum LI, combined witli the observation that vinyl chloride degradation can be competitively inhibited by the addition of ethene or propene, which are both oxidized to the corresponding epoxides, is strong evidence that the initial step in vinyl chloride metabolism is indeed catalyzed by alkene monooxygenase (Figure 3) [25]. 

Figure 3. The initial step in vinyl chloride metabolism of M, aurum LI, catalyzed by alkene monooxygenase.

In studying the inhibitory effects of the less reactive l,2-epo]ypropane, it was previously demonstrated that the inhibitory effect on the monooiygenases examined was much stronger than on other physiological functions of the cell [31]. Althouf not examined for strain LI, this is probably also the case with alkene monooxygenase inactivation by chlorooxirane. 

Alkene monooxygenase (AMO) from Rhodococcus rhodochrous B-276 (also known as Nocardia corallina) is a multicomponent oxygenase that catalyzes the stereoselective insertion of an oxygen atom from O2 into aliphatic alkenes, yielding the corresponding chiral epoxides (Table 1) [151], This reaction is the first step in the pathway of the alkene metabolism. AMO utilizes substrates ranging from C3-... 

Gallagher SC, Cammack R, Dalton H. 1997. Alkene monooxygenase from Nocardia corallina B-276 is a member of the class of dinuclear iron proteins capable of stereospecific epoxygenation reactions. Eur JBiochem 247 635-641. 

Zhou NY, Jenkins A, Chion C, Leak DJ. 1998. The alkene monooxygenase from Aon-thobacter Vy2 is a binuclear non-haem iron protein closely related to toluene 4-monooxygenase. FEBS Lett 430 181-185. 

Miura A, Dalton H. 1995. Purification and characterization of the alkene monooxygenase from Nocardia corallina B-276. Biosci Biotechnol Biochem 59 853-859. 

Saeki H, Akira M, Furuhashi K, AverhoffB, Gottschalk G. 1999. Degradation of tri-chloroethene by a hnear-plasmid-encoded alkene monooxygenase in Rhodococcus corallinus Nocardia corallina) B-276. Microbiology-UK 145 1721-1730. 

Smith TJ, Lloyd JS, Gallagher SG, Fosdike WLJ, Murrell JG, Dalton H. 1999. Heterologous expression of alkene monooxygenase from Rhodococcus rhodochrous B-276. Eur J Biochem 260 446 52. 

Saeki H, Furuhashi K. 1994. Gloning and characterisation of a Nocardia corallina B-276 gene cluster encoding alkene monooxygenase. J Ferment Bioeng 78 399 06. 

Fosdike WLJ, Smith TJ, Dalton H. 2005. Adventitious reactions of alkene monooxygenase reveal common reaction pathways and component interactions among bacterial hydrocarbon oxygenases. F 557272 2661-2669. 

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