Pseudomonas species

Pseudomonads also have the abiUty for xenobiotic metaboHsm and are capable of carrying out diverse sets of chemical reactions. Pseudomonas species is used ia the commercial productioa of acrylamide (qv) (18). Several operoas iavolved ia the metaboHsm of xeaobiotic compouads have beea studied. Use of Pseudomonads for the clean up of the environment and for the production of novel chemical iatermediates is likely to be an area of active research ia the 1990s. 

An approach to the construction of Fe(II)-binding agent pyrimine 40, isolated from Pseudomonas species, employed the bis-homophenylalanine 38. Initiation of the Boekelheide reaction with TFAA and hydrolysis gave the advanced intermediate 39 that provided access to the natural product. 

The first step in the complete biodegradation of primary alcohol sulfates seems to be the hydrolysis to yield alcohol. Sulfatases are able to hydrolyze primary alcohol sulfates. Different authors have isolated and used several sulfia-tase enzymes belonging to Pseudomonas species. The alcohol obtained as a result of the hydrolysis, provided that dehydrogenases have been removed to avoid the oxidation of the alcohol, was identified by chromatography and other methods [388-394]. The absence of oxygen uptake in the splitting of different primary alcohol sulfates also confirms the hydrolysis instead of oxidation [395, 396]. The hydrolysis may acidify the medium and stop the bacterial growth in the absence of pH control [397-399]. 

Table 1.5 I nfluence ofthe organic solvent on the enantioselectivity of the lipase PS (from Pseudomonas species) in the kinetic resolution of racemic trans-sobrerol (10).

However, whatever the mechanism of action is, the effect of solvents on enzyme selectivity is sometimes really dramatic. For example, Hrrose et al. [42] reported that in the Pseudomonas species lipase-catalyzed desymmetrization of prochiral... 

Lipases from C. antarctica and P. cepacia showed higher enantioselectivity in the two ionic liquids l-ethyl-3-methylimidazolium tetrafluoroborate and l-butyl-3-methylimidazolium hexafluoroborate than in THE and toluene, in the kinetic resolution of several secondary alcohols [49]. Similarly, with lipases from Pseudomonas species and Alcaligenes species, increased enantioselectivity was observed in the resolution of 1 -phenylethanol in several ionic liquids as compared to methyl tert-butyl ether [50]. Another study has demonstrated that lipase from Candida rugosa is at least 100% more selective in l-butyl-3-methylimidazolium hexafluoroborate and l-octyl-3-nonylimidazolium hexafluorophosphate than in n-hexane, in the resolution of racemic 2-chloro-propanoic acid [51]. 

The principal methods for the hydrolase-promoted synthesis of enantiomerically pure alcohols are depicted in Figure 6.44. Biocatalytic acylation and alcoholysis have been reviewed recently [116,117]. Lipases, esterases, and proteases catalyze these reactions, but CAL-B [118-120], CRL [121,122], and diverse lipase preparations from Pseudomonas species are common place. 

A-Acetimidoyl groups have been found in several LPS from Pseudomonas species. It is generally N-3 of a 2,3-diamino-2,3-dideoxyhexuronic acid residue, as in 43, that carries this group, which was originally mistaken for an imidazoline grouping. It has also been found linked to 2-amino-2,6-di-... 

Tetrodotoxin (TTX) and saxitoxin (STX) are potent sodium channel blockers that are found in phylogenetically diverse species of marine life. The wide distribution of TTX and STX has resulted in speculation that bacteria are the source of these toxins. Recently, investigators have reported isolation of marine bacteria, including Vibrio Alteromonas, Plesiomonas, and Pseudomonas species, that produce TTX and STX. This chapter details the methods and results of research to define bacterial sources of TTX and STX. 

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. - - ... 

Phenol is an important intermediate in the anaerobic degradation of many complex and simple aromatic compounds. Tschech and Fuchs proposed that the carboxylation of phenol to 4-hydroxybenzoate is the first step in the degradation of phenol under denitrifying conditions. However, 4-hydroxybenzoate is not detected in the cultures or cell extracts of the denitrifying Pseudomonas species in the presence of CO2 and phenol, but it is detected if phenol is replaced by phenolphosphate. In contrast, 4-hydroxybenzoate is readily detected as an intermediate of phenol degradation in the iron-reducing bacterium GS-15, and 4-hydroxybenzoate may prove to be a common intermediate in the anaerobic transformation. Thus, in anaerobic degradation of phenolic compounds, it has been postulated that carboxylation reactions may play important roles. 

Monticello DJ, D Bakker, WR Finnerty (1985) Plasmid-mediated degradation of dibenzothiophene by Pseudomonas species. Appl Environ Microbiol 49 756-760. 

Smith MG, RJ Park (1984) Effect of restricted aeration on catabolism of cholic acid by two Pseudomonas species. Appl Environ Microbiol 48 108-113. 

Firestone MK, JM Tiedje (1975) Biodegradation of metal-nitrilotriacetate complexes by a Pseudomonas species mechanism of reaction. Appl Microbiol 29 758-764. 

Harris R, CJ Knowles (1983) Isolation and growth of a Pseudomonas species that utilizes cyanide as a source of nitrogen. J Gen Microbiol 129 1005-1011. 

Klecka GM, DT Gibson (1979) Metabolism of dibenzo[l,4]dioxan by a Pseudomonas species. Biochem J180 639-645. 

Wilkinson SG (1968) Studies on the cell walls of pseudomonas species resistant to ethylenediaminetetra-ace-tic acid. J Gen Microbiol 54 195-213. 

Jones JG, E Bellion (1991) In vivo C and N NMR studies of methylamine metabolism in Pseudomonas species MA. J Biol Chem 266 11705-11713. 

Kersten PJ, S Dagley, JW Whittaker, DM Arciero, ID Lipscomb (1982) 2-Pyrone-4,6-dicarboxylic acid, a catabolite of gallic acids in Pseudomonas species. J Bacteriol 152 1154-1162. 

Markus A, D Krekel, E Lingens (1986) Purification and some properties of component A of the 4-chlorophenyl-acetate 3,4-dioxygenase from Pseudomonas species strain CBS. J Biol Chem 261 12883-12888. 

Goldman P, GWA Milne, MT Pignataro (1967) Fluorine containing metabolites formed from 2-fluorobenzoic acid by Pseudomonas species. Arch Biochem Biophys 118 178-184. 

Takenaka S, S Mnrakami, R Shinke, K Hatakeyama, H Ynknwa, K Aoki (1997) Novel genes encoding 2-aminophenol 1,6-dioxygenase from Pseudomonas species AP-3 growing on 2-aminophenol and catalytic properties of the pnrified enzyme. J Biol Chem 212 14727-14732. 

Blehert DS, KL Knoke, BG Fox, GIT Cambliss (1997) Regioselectivity of nitroglycerine denitration by flavoprotein nitroester reductases purified from two Pseudomonas species. J Bacterial 179 6912-6920. 

Pseudozan is an exopolysacchaiide produced by a Pseudomonas species. It has high viscosities at low concentrations in formation brines, forms stable solutions over a wide pH range, and is relatively stable at temperatures up to 65° C. The polymer is not shear degradable and has pseudoplastic behavior. The polymer has been proposed for enhanced oil-recovery processes for mobility control [1075]. 

Total bacteria Total fungi and yeasts Pseudomonas species Enterobacteriaceae Spore formers... 

The types of microorganisms found in various products are Pseudomonas species, including Pseudomonas aeruginosa, Salmonella, species, Staphylococcus aureus, and Escherichia coli. The USP and other pharmacopoeias recommend certain classes of products to be tested for specified microbial contaminants, e.g., natural plant, animal, and some mineral products for the absence of Salmonella species, suspensions for the absence of E. coli, and topically administered products for the absence of P. aeruginosa and S. aureus. Emulsions are especially susceptible to contamination by fungi and yeasts. Consumer use may also result in the introduction of microorganisms. For aqueous-based products, it is therefore mandatory to include a preservative in the formulation in order to provide further assurance that the product retains its pharmaceutically acceptable characteristics until it is used by the patient. 

Work on the fermentation of microbial polysaccharides started in the mid 1970 s, with the aim of producing improved polymers. Many thousands of samples were screened for microorganisms which produced viscous polymers. Out of over 2000 such slime producing organisms isolated, only one, identified as a Pseudomonas species, now NCIB 11592, seemed to produce a polymer with interesting new properties. 

Monticello, D. J. BAkker, D., and Finnerty, W. R., Plasmid-mediated degradation of diben-zothiophene by Pseudomonas species. Applied and Environmental Microbiology, 1985.49(4) p. 756. 

---