Pyrrolnitrin = antibiotic

The best-studied system producing antibiotics in the rhizosphere are fluorescent pseudomonads, producing up to seven different compounds, as summarized in Fig. 9 2-hydroxyphenazine-l-carboxylate, phenazine-l-carboxylate, 2-hydroxy-phenazine, pyrrolnitrin, pyocyanine, 2.4-diacetylphloroglucinol. and pyoluteorin (48). Nine genes have been identified in the synthesis of phenazine-1-carboxylic... 

Furthermore, the preparation of the antibiotic Pyrrolnitrine by oxidation of the amino-functionalized precursor with the chloroperoxidase from Pseudomonas pyrrocinia was reported (Eq. 13) [155]. The mechanism of this peroxidase-catalyzed N-oxidation has not been elucidated. 

El-Banna N, Winkelmann G (1998) Pyrrolnitrin from Burkholderia cepacia. Antibiotic Activity Against Fungi and Novel Activities Against Streptomycetes. J Appl Microbiol 85 ... 

Sako M, Kihara T, Tanisaki M, Maki Y, Miyamae, Azuma T, Kohda S, Masugi T (2002) Novel Photodegradation of the Antifungal Antibiotic Pyrrolnitrin in Anhydrous and Aqueous Aprotic Solvents. J Org Chem 67 668... 

S. pyrocinia produces [118] an antifungal antibiotic pyrrolnitrin (140) active against mycobacteria. The antimycobacterial activity can be well correlated with the presence of the halogen and nitro group in the aromatic ring. 

Other peroxidases, albeit non-heme, are able to catalyze similar oxidations. CPO from Pseudomonas pyrrocinia has been successfully employed for the preparation of the antibiotic pyrrolnitrine [60]. The amino group of the precursor molecule is directly transformed into a nitro group by the CPO active species (Fig. 6.4b). 

The antifungal antibiotic pyrrolnitrin [3-chloro-4-(2-nitro-3-chlorophenyl)pyrrole] was brominated at the 2-position of the pyrrole moiety by bromoperoxidase from Streptomyces phaeochromogenes. Pyrrolnitrin was chlorinated at the 2-position and at the 2,5-positions of the pyrrole system by perhydrolases from Pseudomonas pyrrocinia and Streptomyces aureofaciens. The corresponding bromo-derivatives were also obtained with these enzymes f54f... 

Antibiotics such as pyoluteorin, pyrrolnitrin, phenazine-l-carboxylate, and 2,4-diacetylphloroglucinol are produced in the spermosphere and rhizosphere and play an important role in suppression of soil-borne plant pathogens. Suppression in a number of cases studied correlates with the production in the soil of the antibiotics. 

The pyrrole ring, although not very common in nature, occurs in some very important natural products. A few antibiotics contain a pyrrole ring, one of the simplest is pyrrolnitrin 22 ... 

While it has been well documented that inorganic phosphate depresses production of many antibiotics, it has also been shown to stimulate or enhance the production of others. The first reported use of high levels of inorganic phosphate for antibiotic production was in 1964, when Arima reported the production of pyrrolnitrin from Pseudomonas fluorescens [96]. This antidermatophytic antibiotic was discovered when an accidental addition of 10 times as much inorganic phosphate as intended subsequently resulted in not only higher production of pyrrolnitrin, but more reproducible results than previous methods had yielded. The production of globopeptin was increased 2.5 fold by addition of magnesium phosphate [97]. 

Antibiotic pyrrolnitrin Pseudomonas multivorans Toluene Mabe et al, 1970... 

Saphire , Syngenta) [164] have been developed from the photo-unstable and chlorine-containing natural antibiotic pyrrolnitrin (75 Pyroace , Fujisawa) that was first isolated from Pseudomonas pyrrocinia [165] (Fig. 35.18, Table 35.11). 

Fig. 35.18. From natural antibiotic pyrrolnitrin (75) to the pyrrole fungicides fenpiclonil (76) and fludioxonil (77).

An example of an electrophilic aromatic halogenation occurs in the biosynthesis of the antifungal antibiotic pyrrolnitrin. 

The biosynthesis of the antifungai antibiotic pyrrolnitrin begins with enzyme-cataiyzed chiorination of the benzene ring of... 

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