Pseudomonas aureofaciens

Phenazines — This large class of compounds includes more than 6,000 natural and synthetic representatives. Natural phenazines are secondary metabolites of certain soil and marine microorganisms. The main phenazine producers are Pseudomonas and Streptomyces species. Pseudomonas strains produce the most simple phenazines tubermycin B (phenazine-1-carboxylic acid), chlororaphine, pyocyanin, and iodinine. Pyocyanin is a blue pigment while chlororaphine is green both are produced by Pseudomonas aeruginosa. They can be seen in infected wounds of animal and human skins. Iodinine is a purple phenazine produced by Pseudomonas aureofaciens. 

Lubbe C, K-H van Pee, O Salcher, F Lingens (1983) The metabolism of tryptophan and 7-chlorotryptophan in Pseudomonas pyrrocinia and Pseudomonas aureofaciens. Zphysiol Chem 364 447-453. 

L. A. Harrison, L. Lctendre, P. Kovacevich, E. Pierson, and D. Weller, Purilication of an antibiotic effective against Gaeumannomyces graininis var. tritici produced by a biocontrol agetU, Pseudomonas aureofaciens. Soil Biology and Biochemistry 2.5 215 (1993). 

DMP Pseudomonas fluorescens, Pseudomonas aureofaciens and Sphingomonas paucimobilis Complete Wang et al. (2003a)... 

Beiderbeck H, Risse D, Budzikiewicz H, Taraz K (1999) A New Pyoverdin from Pseudomonas aureofaciens. Z Naturforsch 54c 1... 

Glockner, A. B., Jiingst, A., and Zumft, W. G. (1993). Copper-containing nitrite reductase from Pseudomonas aureofaciens is functional in a mutationally cytochrome cd,-free background (NirS ) of Pseudomonas stutzeri. Arch. Microbiol. 160, 18-26. 

Zumft, W. G., Gotzmann, D. J., and Kroneck, P. M. H. (1987). Type 1, blue copper proteins constitute a respiratory nitrite-reducing system in Pseudomonas aureofaciens. Eur. J. Biochem. 168, 301-307. 

Several phenazine derivatives, e.g. phenazin-2-ol, phenazine-l-carboxylic acid, 2-hydroxy-phenazine-1-carboxylic acid, phenazine-2,3-diol, and 2,3-dihydroxyphenazine-l-carboxylic acid have been isolated from Pseudomonas aureofaciens. 

Further support for the conclusion that two molecules of shikimic acid are involved in phenazine biosynthesis comes from the incorporation of >-[1,6,7,- CaJshikimic acid [as (134)] into phenazine-1-carboxylic acid (138) in Pseudomonas aureofaciens with close to a fifth of the activity present in the carboxy-group, as required if two molecules of shikimic acid are involved [however, the same result would have been obtained if only one molecule of shikimic add was implicated provided that a symmetrical intermediate of type (139) was also involved in the elaboration of (138)]. 

Bromoperoxidase has been isolated from Pseudomonas aureofaciens ATCC 15926, also displays peroxidase and catalase activities, and contains ferriprotoporphyrin IX (van Pee and Lingens 1985). Four different bromoperoxidases have been isolated from Streptomyces griseus (Zeiner et al. 1988). Only one of them, however, contains ferriprotoporphyrin IX and displays peroxidase and catalase activities. This illustrates that there are two different groups of enzymes, one of which lacks heme prosthetic groups. 

Most proteins with type 1 copper centers are blue, although the nitrite reductases from Achromobacter cycloclastes, Alcaligenes faecalis, and Pseudomonas aureofaciens, are green [26,27]. This is probably caused by a distortion of the type 1 copper center, although the interrelation of distortion and absorption properties of the copper centers have not yet been clarified [27]. 

Phenazines and Phenoxazlnones.— A preliminary report (cf. Vol. 9, p.28) concerning the incorporation of phenazine-1,6-di-carboxylic acid (113) and its methyl ester (114) into phenazine-1-carboxylic acid (115) in Pseudomonas aureofaciens, and of (113) into lomofungin (112) in Streptomyces lomodensis, has appeared in full (cf. Vol. 10, p.28 Vol. 12, p.29). In addition,(111) has been isolated from an extract of S, lomodensis cultures after the extract had been treated with excess diazomethane. The (111) incorporated label from radioactive (113). It is reasonable to conclude from this that (110) (or a methyl ester ) is produced from (113) as an intermediate in the biosynthesis of lomofungin (112). 

This general approach of feeding precursors can also be used just to increase levels of the naturally occurring metabolite by supplementing the culture with the natural precursors. This is illustrated by the simple example of pyrrolnitrin production by Pseudomonas aureofaciens, which was increased significantly... 

Hamill, R. L., Elander, R. P., Mabe, J. A., and Gorman, M. (1970) Metabolism of tryptophan by Pseudomonas aureofaciens III. Production of substituted pyrrolnitrins from tryptophan analogues. Appl Microbiol 19,721—725. 

Pyrrolnitrin.—Pyrrolnitrin (52), a metabolite of Pseudomonas aureofaciens, is known to derive from tryptophan and the D-isomer is a more effective precursor than L-tryptophan. The amino-compound (51) has been isolated from Ps. aureofaciens and is efficiently incorporated into pyrrolnitrin. A biosynthetic pathway (Scheme 7) has been proposed. 

Cultures of Pseudomonas aureofaciens and P. chlororaphis (neither of which reduced N2O to N2) were exposed to N02 and several concentrations of NO (4). Increasing NO was noted with increasing concentrations of NO. As shown in Figure 7, NO production occurred at the expense of N2 production and continued until N02" was exhausted. At this time, NO consumption began and appeared to give rise to additional N— N20. We feel this data is evidence that either NO is an intermediate or is in rapid equilibrium with an enzyme-bound species. 

Pyrrolnitrin.—Pyrrolnitrin (109) is a metabolite of Pseudomonas aureofaciens and is derived from tryptophan. The amino-compound (108) is naturally occurring, and (107) has now also been isolated." This, taken together with evidence from feeding experiments (cf. ref. 4, p. 28), indicates the pathway shown in Scheme 4.3-Chloroanthranilic acid and 7-chloroindoleacetic acid have also been isolated from P. aureofaciens ... 

It has been claimed that dimethyl phenazine-1,6-dicarboxylate (128) is a precursor for 1-carboxyphenazine in Pseudomonas aureofaciens cf. ref. 8. This claim has been disputed careful checking showed that neither (128) nor the corresponding acid (129) was incorporated into phenazines produced by this organism. This has been supported by the results of other workers, who have found that (128) is metabolically inert in P. aureofaciens. Moreover, neither (129) nor (128) was incorporated into phenazines in P. phenazinium. On the other hand, efficient incorporations have been recorded of (129), but not of (128), into iodinin (127) and related phenazines in three actinomycetes, i.e. Streptomyces thioluteus, Microbispora amethystogenes, and M parva ... 

There are two main types of NiRs involved in the reduction of nitrites, namely, the heme-containing cytochrome cdj NiR which was obtained and first purified from Thiosphaera pantotropha (261). The second kind of NiR is the copper-containing NiR which was first isolated from Alcaligenes xylosoxidans NCIB 11015, a bacterial isolated from a soil in Japan. Other Cu NiR have been isolated from, Achromohacter cycloclastes, Alcaligenes faecalis S-6, Bacillus halodenitrificans, Haloferax denitrificans, Nitrosomonas europaea, Pseudomonas aureofaciens, Rhodobacter sphaeroides, and Hyphomicrobium sp. (262 and references thereinj. In mammalian systems, nitrites are reduced by deoxyHb (263) and by ferrous myoglobin (264,265) to nitric oxide. In synthetic iron porphyrins. Ford and coworkers have demonstrated how nitrites inhibit the reductive nitrosylation process by forming ferric-nitrites species (266). 

H. Budzikiewicz, H. Scholl, W. Neuenhaus, G. Pulverer, and H. Korth, Dialkylresorcine aus Pseudomonas aureofaciens,... 

The most intensively studied haloperoxidases are the chloroperoxidase from the mold Caldariomyces fumago [1322] and bromoperoxidases fi om algae [1764] and bacteria such as Pseudomonas aureofaciens [1765], Ps. pyrrocinia [1766], and Streptomyces sp. [1767]. The only iodoperoxidase of preparative use is isolated from horseradish root [1768]. A haloperoxidase isolated from milk has been reported to be useful for the formation of halohydrins [1769]. 

Hydroxyphenazine-l-carboxylic acid (li) and 2-hy-droxyphenazine (lb) are believed to be derived sequentially from phenazine-1-carboxylic acid (Ih) via known biotransformation reactions, presumably via an arene oxide intermediate (Scheme 3). In Pseudomonas aureofaciens, an NADPH-dependent reductase is responsible for the hydroxylation to form li, whereas the subsequent decarboxylation to give lb occurs spontaneously and nonenzymatically. ... 

Pyrrolnitrin (7.76), a Pseudomonas aureofaciens metabolite, is formed from tryptophan with loss only of the carboxy-group in a biosynthetic sequence which obviously involves fracture of the indole nucleus. The... 

Analogous feeding experiments with Pseudomonas aureofaciens established that (87) but not (88) was utilised in the formation of 2-hydroxyphenazine-l-carboxylic acid (94) and 2-hydroxyphena-zine (95). These results were interpreted as showing that both of these phenazine metabolites (94 and 95) are metabolites of phenazine-1-carboxylic acid (87) and are formed as outlined above. 

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