Bioconversion of car-3-ene by a dioxygenase of Pleurotus sapidus

Lehnert, Nicole; Krings, Ulrich; Sydes, Daniel; Wittig, Maximilian; Berger, Ralf G.

doi:10.1016/j.jbiotec.2011.06.007

Cited by 13 publications

(19 citation statements)

References 28 publications

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“…(+)-Valencene, a sesquiterpene from orange oil, was converted to (+)-nootkatone and nootkatols [26]. Lyophilisates of P. sapidus catalyzed the oxyfunctionalization of R-(+)-limonene to carvone [40], of˛-pinene to verbenone/ol [41] and of (+)-car-3-en to car-3-ones/ols [42] as well as the transformation of various cycloalkenes to the corresponding enones [43]. This promiscuity calls for a biotechnological application to produce other bioactive or fragrant terpenoids.…”

Section: Resultsmentioning

confidence: 99%

LOXPsa1, the first recombinant lipoxygenase from a basidiomycete fungus

Plagemann

Zelena

Arendt

et al. 2013

Journal of Molecular Catalysis B: Enzymatic

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Section: Resultsmentioning

confidence: 99%

LOXPsa1, the first recombinant lipoxygenase from a basidiomycete fungus

Plagemann

Zelena

Arendt

et al. 2013

Journal of Molecular Catalysis B: Enzymatic

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“…Already in the 1960s, the aerobic metabolism of several monoterpenes (limonene and α -pinene) was described for soil pseudomonads and the fungus Aspergillus niger [4]. Pseudomonads also use the acyclic citronellol [5,6] and Pleurotus sapidus was found to transform the bicyclic Δ 3 -carene [7]. Limonene may be an intermediate in the metabolism of bicyclic [8] and acyclic monoterpenes [9].…”

Section: Introductionmentioning

confidence: 99%

The oxygen-independent metabolism of cyclic monoterpenes in Castellaniella defragrans 65Phen

et al. 2014

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BackgroundThe facultatively anaerobic betaproteobacterium Castellaniella defragrans 65Phen utilizes acyclic, monocyclic and bicyclic monoterpenes as sole carbon source under oxic as well as anoxic conditions. A biotransformation pathway of the acyclic β-myrcene required linalool dehydratase-isomerase as initial enzyme acting on the hydrocarbon. An in-frame deletion mutant did not use myrcene, but was able to grow on monocyclic monoterpenes. The genome sequence and a comparative proteome analysis together with a random transposon mutagenesis were conducted to identify genes involved in the monocyclic monoterpene metabolism. Metabolites accumulating in cultures of transposon and in-frame deletion mutants disclosed the degradation pathway.ResultsCastellaniella defragrans 65Phen oxidizes the monocyclic monoterpene limonene at the primary methyl group forming perillyl alcohol. The genome of 3.95 Mb contained a 70 kb genome island coding for over 50 proteins involved in the monoterpene metabolism. This island showed higher homology to genes of another monoterpene-mineralizing betaproteobacterium, Thauera terpenica 58EuT, than to genomes of the family Alcaligenaceae, which harbors the genus Castellaniella. A collection of 72 transposon mutants unable to grow on limonene contained 17 inactivated genes, with 46 mutants located in the two genes ctmAB (cyclic terpene metabolism). CtmA and ctmB were annotated as FAD-dependent oxidoreductases and clustered together with ctmE, a 2Fe-2S ferredoxin gene, and ctmF, coding for a NADH:ferredoxin oxidoreductase. Transposon mutants of ctmA, B or E did not grow aerobically or anaerobically on limonene, but on perillyl alcohol. The next steps in the pathway are catalyzed by the geraniol dehydrogenase GeoA and the geranial dehydrogenase GeoB, yielding perillic acid. Two transposon mutants had inactivated genes of the monoterpene ring cleavage (mrc) pathway. 2-Methylcitrate synthase and 2-methylcitrate dehydratase were also essential for the monoterpene metabolism but not for growth on acetate.ConclusionsThe genome of Castellaniella defragrans 65Phen is related to other genomes of Alcaligenaceae, but contains a genomic island with genes of the monoterpene metabolism. Castellaniella defragrans 65Phen degrades limonene via a limonene dehydrogenase and the oxidation of perillyl alcohol. The initial oxidation at the primary methyl group is independent of molecular oxygen.

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“…Biotransformations of (A) heme-thiolate peroxygenases UPO’s [41,43,44] and (B) non-heme iron lipoxygenase-type dioxygenases (LOX) [60,61,79,80]. …”

Section: Figurementioning

confidence: 99%