Microbial Halogenation

Neidleman, Saul L.

doi:10.3109/10408417509108755

Cited by 38 publications

(23 citation statements)

References 32 publications

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“…In such species CH $ Cl is involved as a methyl donor in the biosynthesis of O-methyl phenols such as veratryl alcohol (Harper et al, , 1996Coulter et al, 1993a). The participation of CH $ Cl in fungal primary metabolism is the first unequivocal evidence supporting the proposal of Neidleman (1975) that some halometabolites may have a role as transient intermediates in the biosynthesis of nonhalogenated products.…”

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confidence: 99%

Emissions, biogenesis and metabolic utilization of chloromethane by tubers of the potato (Solanum tuberosum)

et al. 1999

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CH $ Cl emissions by freshly harvested tubers of 61 potato cultivars ranged from less than 4 to 650 ng g −" f. wt d −" . In experiments with Anna, the cultivar displaying the highest release rate, maximum emission of CH $ Cl occurred at 20mC but the rate diminished after 48 h, a decrease due in part to inhibition of CH $ Cl release by the accumulation of CH $ Cl in the headspace. In 1995 and 1996, CH $ Cl emission by tubers was first detectable 6 wk before the normal harvest date. If tubers were stored at 20mC immediately following harvest, release attained a maximum of 350 ng g −" f. wt d −" about 4 d after harvest, falling to less than 4 ng g −" f. wt d −" within 3 wk of harvest. On storage at 6mC post-harvest, maximum release of CH $ Cl (c. 600 ng g −" ) was delayed until 5 wk after harvest and release fell below 4 ng g −" f. wt d −" after 200 d. Release of CH $ Cl was not significantly affected by cutting or bruising tuber tissue, and CH $ Cl biosynthesis occurred in both core and superficial tissues of the tuber. The Smethyl group of either L-or D-methionine acted as a precursor of CH $ Cl in sliced tubers, but the methylating system was specific for Cl − . An isotope dilution technique using C#H $ Cl demonstrated that the amount of CH $ Cl metabolized by the intact tuber was approximately 36% of the net release. However, investigations with "%CH $ Cl showed that only a small proportion (7%) of the CH $ Cl metabolized was fixed in involatile form in the tuber. In both skin and core tissues, fixed "%C was located primarily (80%) in the fraction soluble in phosphate buffer, but the specific activity of skin tissue was about twice that of core tissue. Autoradiography demonstrated that "%C fixation in the tuber was greatest within the lenticels, possibly indicating a microflora adapted to use the locally high concentrations of CH $ Cl. Significant "%C fixation was also associated with the periderm but was not attributable to labelling of the O-methyl groups of the phenolic components of suberin. Within the core of the tuber, "%C fixation was located primarily in the phloem, pith and medullary rays.

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confidence: 99%

Emissions, biogenesis and metabolic utilization of chloromethane by tubers of the potato (Solanum tuberosum)

et al. 1999

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“…The incorporation of chlorine during the biosynthesis of 7-chlorotetracycline is believed to be catalyzed by a chloroperoxidase (12). However, only a brominating enzyme, a bromoperoxidase, could be isolated from this strain (18).…”

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Molecular cloning and high-level expression of a bromoperoxidase gene from Streptomyces aureofaciens Tü24

Pée

1988

J Bacteriol

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A bromoperoxidase gene was cloned from Streptomyces aureofaciens Tu24 into Streptomyces lividans TK64 by using the promoter-probe vector pIJ486. Subcloning of DNA from the original, unstable clone allowed the gene to be localized to a 1.7-kilobase (kb) fragment of DNA. Southern blotting showed that the cloned 1.7-kb insert hybridized to a 4.3-kb fragment in an SstI digest of S. aureofaciens Tu24 total DNA. The 1.7-kb insert was shown to code for a protein with the electrophoretic properties of the subunits of the nonheme bromoperoxidase isolated from S. aureofaciens Tu24.-The protein produced by S. lividans TK64 transformed with pHM621, which contained an 8.0-kb insert, was shown to be identical to the S. aureofaciens Tu24 bromoperoxidase in terms of its electrophoretic mobility on denaturing and nondenaturing polyacrylamide gels and its NH2-terminal amino acid sequence. The bromoperoxidase was overproduced (up to 180 times) by S.lividans TK64 containing pHM621. Based on the heat stability of the S. aureofaciens Tu24 bromoperoxidase, a new and simple purification procedure with very high yields was developed.Streptomyces aureofaciens Tu24 produces the antibiotic 7-chlorotetracycline. The incorporation of chlorine during the biosynthesis of 7-chlorotetracycline is believed to be catalyzed by a chloroperoxidase (12). However, only a brominating enzyme, a bromoperoxidase, could be isolated from this strain (18). Bromoperoxidases have been isolated from other chlorometabolite-producing bacteria as well (16,17,20). The only bacterial chloroperoxidase known until now was detected in Pseudomonas pyrrocinia (2). This enzyme was detected as a bromoperoxidase by the monochlorodimedone assay developed by Hager et al. (2). Monochlorodimedone was not chlorinated by the chloroperoxidase from P. pyrrocinia; however, when indole was used as a substrate, it was chlorinated to 7-chloroindole (21), a substance which is known to be produced by P. pyrrocinia (8). Therefore, it was thought to be possible that the bromoperoxidase isolated from S. aureofaciens Tu24 could be a chloroperoxidase, too, but only if a more "natural" substrate than monochlorodimedone was used. To check this, large amounts of the enzyme are needed, and thus I decided to try to clone the bromoperoxidase gene of S. aureofaciens Tu24. This report describes the cloning of the S. aureofaciens Tu24 bromoperoxidase gene in S. lividans TK64. MATERIALS AND METHODSBacterial strains and culture conditions. S. lividans TK64 and S. lividans TK24 containing the promoter-probe plasmid vector pIJ486 (19) were kindly supplied by D. A. Hopwood, Norwich, England, and S. aureofaciens Tu24 was provided by H. Zahner, Tubingen, Federal Republic of Germany (FRG). These strains were cultured on agar plates containing 2% (wt/vol) soybean flour and 2% (wt/vol) mannitol. This medium was also used as a liquid medium when cells were grown for the production of bromoperoxidase. Other media used were yeast extract-malt extract plus 34% (wt/vol) sucrose (YEME) (1); R2YE medium (14); P medium ...

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“…Biohalogenation is not a rare event in nature, at the moment more than 700 halogenated compounds are knirwn [23]. This is, however, the first report of chlorinated aromatics production by a white-rot fungus.…”

Section: Dlscussionmentioning

confidence: 86%

De‐novo biosynthesis of chlorinated aromatics by the white‐rot fungus Bjerkandera sp. BOS55 Formation of 3‐chloro‐anisaldehyde from glucose

et al. 1992

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The white-rot fungus Bjerkanderu sp. BOSS5 produced de-novo several aromatic metabolites. Bcsidcs vcratryl alcohol and veratraldchyde, compounds which are known to be involved in the ligninolytic system of several other white-rot fungi, other metabolitcs were formed. These included anisaldehyde, 3-chloro.xnisaldchydc and a yet unknown compound containing two chlorine atoms. Additionally GC/MS analysis revealed the production of small amounts ofanisyl alcohol and 3-chloro-anisyl alcohol. After 14 days, tbe extracellular fluid of Ltjerkuttdera l3OS55 contained lOO/tM veratraldehyde and 50,~M 5-chloro-anisaldehyde. This is the first report ofde-novo biosynthesis of simple chlorinated aromatic compounds by a white-rot fungus. Anisaldehyde and 3.chloro-anisaldehyde were also produced by Bjerkatrderrr adusru but not by Pl~ar~e~ocltuerc c/rr_vsospriu/rr.

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Microbial Halogenation

Cited by 38 publications

References 32 publications

Emissions, biogenesis and metabolic utilization of chloromethane by tubers of the potato (Solanum tuberosum)

Emissions, biogenesis and metabolic utilization of chloromethane by tubers of the potato (Solanum tuberosum)

Molecular cloning and high-level expression of a bromoperoxidase gene from Streptomyces aureofaciens Tü24

De‐novo biosynthesis of chlorinated aromatics by the white‐rot fungus Bjerkandera sp. BOS55 Formation of 3‐chloro‐anisaldehyde from glucose

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