Pyocyanin

C. Pyocyanine alkylation). A solution of 2 g. (0.011 mole) of a-hydroxyphenazine in 13.4 g. (10 ml., 0.1 mole) of methyl sulfate (Note 10) is placed in a 250-ml. Erlenmeyer flask fitted with a calcium chloride drying tube and heated at 100° (oil bath) for 10 minutes. The solution is allowed to cool to room temperature, and about 7.5 ml. of dry ether is added. The dark brown solid is filtered on a 7-cm. Eiichner funnel and washed with about ISO ml. of dry ether in several portions (Note 11). 

This series of reactions is essentially the one described by Wrede and Strack. Pyocyanine can also be prepared by the photochemical oxidation of phenazinc methosulfate. ... 

Pyocyanine (l-hydroxy-5-methylphenazinium zwitterion) [85-66-5] M 210.2, m 133 (sublimes and dec on further heating). Crystd from H2O as dark blue needles. Picrate has m 190° dec. 

Aeruginosine A (254) (69JCS(C)2514) and B (255) (61MI2), shown in Scheme 83, are metabolites of the pyocyanine producing Pseudomonas aeruginosa. They are isoconjugate with the odd alternant 1-isopropenyl-anthracene anion (class 13). 

Phenazines — The phenazines are biosynthesized by the shikimic acid pathway, through the intermediate chorismic acid. The process was studied using different strains of Pseudomonas species, the major producers of phenazines. The best-known phenazine, pyocyanine, seems to be produced from the intermediate phenazine-1-carboxylic acid (PCA). Although intensive biochemical studies were done, not all the details and the intermediates of conversion of chorismic acid to PCA are known. In the first step, PCA is N-methylated by a SAM-dependent methyltransferase. The second step is a hydroxylative decarboxylation catalyzed by a flavoprotein monooxygenase dependent on NADH. PCA is also the precursor of phenazine-1-carboxamide and 1-hydroxyphenazine from Pseudomonas species. - - ... 

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. 

Mavrodi DV, RE Bonall, SMK Delaney, MJ Soule, G Phillips, LS Thomashow (2001) Eunctional analysis of genes for biosynthesis of pyocyanin and phenazine-l-carboxamide from Pseudomonas aeruginosa PAGE J Bacterial 183 6454-6465. 

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... 

The leuco form is readily oxidized to a paramagnetic green ion-radical and thence to pyocyanine itself. 

H 0 A-butanoyl-L-homoserine lactone, BHL or C4-HSL Aeromomas hydrophila Aeromonas salmonicida Pseudomonas aeruginosa, Serratia liquefaciens Extracellular protease, biofilm formation. Extracellular protease. Virulence factors - alkaline protease, cyanide, elastase, haemolysin, lectins, pyocyanin, rhaminolipid, RpoS Swarming, protease. 

Naturally occurring phenazines from bacteria have been known since the middle of the nineteenth century [1,2]. The first examples included pyocyanine (1),... 

The same problem occurs with the synthesis of lavanducyanin (65) [85,87] and phenazinomycin (67) [88]. Here, Kitahara et al. used the same approach in that they first generated the phenazine skeleton and performed the AT-allylation as the last step. While the AT-methylation of the unprotected 1-hydroxyphenazine (109) proceeds without any major problems and provides pyocyanin (1) in acceptable yields [89], model experiments already indicate that the allylation of 110 could not be so readily accomplished. As expected, the yields were poor. The only way to bring about the synthesis of 65 is under high-pressure conditions by reaction of 110 with 111, and even so the yield of the natural product remains quite low. Similar problems are encountered with the synthesis of 67 by allylation of 110 with the terpenoid component 112. 

The bacteria Pseudomonas spp. produce tabtoxin and pyocyanine, alkaloids with a relatively powerful biological activity. 

It is important to emphasize that systems in which the lone pair originates at a starred position can be represented by dipolar canonical forms as well as by purely covalent structures and that sometimes these dipolar structures are a better representation of the molecule. Examples of this are the antibiotic pyocyanine (28 29) and the berberine derivative 30+->31, 5 In... 

Claudia J. Nachef was born in Saida, Lebanon. She holds a B.S. degree from the Saint-Joseph University, Lebanon, and a M.S. degree (Doctor Jean-Yves Winum) from the University of Montpellier II, France. She is currently a research assistant at the American University of Beirut (Professor M. J. Haddadin). She worked on sulfonylureas for her M.S. degree and has been working on benzofurazan oxides, quinoxaline 1,4-dioxides, phenazines, and pyocyanins. 

Ferrocene was one of the earliest mediators used [10] but is somewhat hydrophobic so derivatives of the molecule are often employed [39-43]. Ferricyanide can also be used, and the use of MWCNT with this mediator was shown to enhance its effectiveness [33]. Other groups have studied a wide diversity of novel mediator systems such as poly(vinylferrocene-co-acrylamide) dispersed within an alumina nanoparticle membrane [34], ruthenium [35] and osmium [36,37] complexes, and the phenazine pigment pyocyanin, which is produced by the bacteria Pseudomonas aeruginosa [38]. 

K. Ohfuji, N. Sato, N. Hamada-Sato, T. Kobayashi, C. Imada, H. Okuma and E. Watanabe, Construction of a glucose sensor based on a screen-printed electrode and a novel mediator pyocyanin from Pseudomonas aeruginosa, Biosens. Bioelectron., 19 (2004) 1237-1244. 

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