Tetralin (1,2,3,4-tetrahydronaphthalene) is a widely used organic solvent for fats, resins and waxes. It can also be found in many household products like paints, lacquers and shoe polishes. Tetralin absorbed in cells may form toxic hydroperoxides and inhibit bacterial growth in concentrations higher than 100 micromoles/liter. Due to its lipophilic nature, tetralin accumulates in cell membranes resulting in structural and functional changes (Hernaez et al., 2002).
Camphor 5-monooxygenase from Pseudomonas putida PgG 786 and Pseudomonas stutzeri AS39 catalyzes the conversion of tetralin to (R)-1,2,3,4-tetrahydro-1-naphthol. Oxidation of the alcohol yields 1,2,3,4-tetrahydronaphthalone (Grayson et al., 1996). Corynebacterium sp. strain C125 is capable of growing on tetralin as a sole source of carbon. Degradation proceeds via a series of reactions involving hydroxylation, dehydrogenation, extradiol cleavage, and hydrolytic attack (Sikkema et al., 1993) (Hernaez et al., 2002). Tetralin is ultimately converted to pyruvate, an intermediary metabolite, and 7-oxoheptanoate (pimelic semialdehyde). This last compound, in Methanosarcina thermophila, can serve as a precursor to Coenzyme B (Howell et al., 1998).
The following is a text-format Tetralin pathway map. Organisms which can initiate the pathway are given, but other organisms may also carry out later steps. Follow the links for more information on compounds or reactions. This map is also available in graphic format.
Graphical Map (5k) Graphical Map (15k) Tetralin Tetralin Pseudomonas putida PgG 786 Sphingopyxis macrogoltabida TFA Pseudomonas stutzeri AS39 Corynebacterium sp. C125 | | | | | | tetralin | camphor | ring-hydroxylating | 5-monooxygenase | dioxygenase | | | | v v (R)-1,2,3,4- cis-1,2-Dihydroxy-1,2,5,6,7,8- Tetrahydronaphthol hexahydronaphthalene | | | | | (R)-1,2,3,4-tetrahydro- | 1,2-dihydroxy-1,2,5,6,7,8- | naphthol dehydrogenase | hexahydronaphthalene | | dehydrogenase | | | | v v 1,2,3,4-Tetrahydro- 1,2-Dihydroxy-5,6,7,8- naphthalone tetrahydronaphthalene | | | 1,2-dihydroxy-5,6,7,8 | tetrahydronaphthalene | extradiol dioxygenase | | v 4-(2-Oxocyclohexyl)- 2-hydroxy-buta-2,4-dienoate | | | 4-(2-oxocyclohexyl)-2-hydroxy- | buta-2,4-dienoate hydrolase | | v 2-Hydroxydec-2,4-diene- 1,10-dioate | | | 2-hydroxydec-2,4-diene- | 1,10-dioate hydratase | | v (2Z)-2,4-Dihydroxydec-2-enedioate | | | | (2Z)-2,4-dihydroxydec- | 2-enedioate aldolase | | | 7-Oxoheptanoate <------+------> Pyruvate | | | v Intermediary Metabolism (KEGG)
Page Author(s): Jiun-guo Yu, Michael J. Turnbull
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