Pseudomonas cepacia

Regioselective hydrolysis of diesters is a challenging problem ia synthetic chemistry because the side reactions always reduce the yield of desired product. Some Upases are well suited to perform this task. Lipase OF-360 (Meito Sangyo) hydrolyzes diester (55) ia 74% theoretical yield and 93% ee (70). Lipase from Pseudomonas cepacia suspended ia diisopropyl ether saturated with water hydrolyzes triester (56) with a remarkable efficiency and regio- and stereoselectivity (71). 

Of course, the influence of organic solvents on enzyme enantioselectivity is not limited to proteases but it is a general phenomenon. Quite soon, different research groups described the results obtained with lipases [28]. For instance, the resolution of the mucolytic drug ( )-trans-sobrerol (11) was achieved by transesteriflcation with vinyl acetate catalyzed by the lipase from Pseudomonas cepacia adsorbed on celite in various solvents. As depicted in Scheme 1.3 and Table 1.5, it was found that t-amyl alcohol was the solvent of choice in this medium, the selectivity was so high ( >500) that the reaction stopped spontaneously at 50% conversion giving both +)4rans-sobrerol and (—)-trans-sobrerol monoacetate in 100% optical purity [29]. 

Burkholderia cepacia has formerly been known as Pseudomonas cepacia. 

For the kinetic resolution of racemic a-acetoxyamide 6 several native enzymes were used (Scheme 5.5). The native Upases from Pseudomonas cepacia (PCL) and porcine pancreas (PPL) showed the highesL although stiU unsatisfactory, enantios-electivity ( = 5.1 and 3.5, respectively). Upon immobilization into a solgel matrix, the enantioselectivity of PCL was improved significantly to 30.5. The covalent immobilization on Eupergit increased the enantioselectivity even more (34.0) [23]. 

Deoxy-L-mannose (L-rhamnose) is common, but D-rhamnose has only been found in some 0-antigens, as in that of Pseudomonas cepacia IMV 3181, which is a homopolysaccharide containing both a- and y -pyranosyl residues. 

Deoxy-L-galactose (L-fucose) is common, and has only been found as the a- or )3-pyranoside. The rare D-fucose has, however, been found both as a-pyranoside, in the LPS frorn Pseudomonas cepacia serotypes B and E, and as a-furanoside, in the cell-wall antigen from Eubacterium saburreum L 452 and the O-antigens from different strains of Psuedomonas syrin-gae The a-furanoside, as in 3, has a cis relationship between the aglycon and OH-2. The corresponding P form has not yet been found. 6-Deoxy-o-and -L-talose are components of the extracellular polysaccharides from some strains of Butyrivibrio fibrisolvens and of the LPS from some strains of E. coli respectively. 

Burkholderia (formeriy Pseudomonas) cepacia is intrinsically resistant to a number of biocides, notably benzalkonium chloride and chlorhexidine. Again, the outer membrane is likely to act as a permeability barrier. By contrasL Ps. stutzeri (an organism implicated in eye infections caused by some cosmetic products) is invariably intrinsically sensitive to a range of biocides, including QACs and chlorhexidine. This organism contains less wall muramic acid than other pseudomonads but it is imclear as to whether this could be a contributory factor in its enhanced biocide susceptibility. 

Later, in a modification to the above system, we reported the use of an indenylruthenium complex 2 as a racemization catalyst for the DKR of secondary alcohols, which does not require ketones but a weak base hke triethylamine and molecular oxygen to be achvated. The DKR with 2 in combination with immobilized Pseudomonas cepacia lipase (PCL, trade name. Lipase PS-C ) was carried out at a lower temperature (60°C) and provided good yields and high optical purities (Table 2). This paved the way for the omission of ketones as... 

C-chiral racemic y-hydroxy sulfides were also resolved using PEL under kinetic resolution conditions. The products were transformed into optically active 3-(alkanesulfonyloxy)thiolane salts (Scheme 1). Similarly, 1,2-cyclic sulfite glycerol derivatives cis and trans) were resolved into enantiomers via a Pseudomonas cepacia-catalysed acylation with vinyl butyrate. The E values depended on the solvent used and varied from 2 to 26. ... 

Enzymes PPL, lipase from Pseudomonas fluorescens F-AP, lipase from Rhizopus orizae AP-6, lipase from Aspergillus niger, SP-254, lipase from Aspergillus oryzae P-2, Chirazyme WCPC, whole cell cultures of Penicillium citrinum WCPFL, whole cell cultures of Pseudomona fluorescens CAL-B, lipase from Candida antarctica B PS-C, lipase from Pseudomonas cepacia GCL, lipase from Geotrichum candidum. n.r. not reported. 

Lipase ANL, lipase from Aspergillus niger, BCL, lipase from Burkholderia cepacia (formerly Pseudomonas cepacia) CAL-B, lipase from Candida antarctica B PPL, lipase from Pseudomonas fluorescens PPL, pig pancreatic lipase. 

Toluene monooxygenases provide alternatives to dioxygenation, and the ortho-mono-oxygenase in Burkholderia (Pseudomonas) cepacia G4 has been shown to be carried... 

Batie CJ, E LaHaie, DP Ballou (1987) Purification and characterization of phthalate oxygenase and phthalate oxygenase reductase from Pseudomonas cepacia. J Biol Chem 262 1510-1518. 

Fetzner S, R Muller, and E Lingens (1992) Purification and some properties of 2-halobenzoate 1,2-dioxygenase, a two-component enzyme system from Pseudomonas cepacia 2CBS. J Bacterial 174 279-290. 

Shields MS, MJ Reagin, RR Gerger, R Campbell, C Somerville (1995) TOM, a new aromatic degradative plasmid from Burkholderia (Pseudomonas) cepacia G4. Appl Environ Microbiol 61 1352-1356. 

Folsom BR, PJ Chapman, PH Pritchard (1990) Phenol and trichloroethylene degradation by Pseudomonas cepacia G4 kinetics and interactions between substrates. Acinetobacter sp. strain A-CBl. Appl Environ Microbiol 56 1279-1285. 

Jin G, AJ Englande (1997) Biodegradation kinetics of carbon tetrachloride by Pseudomonas cepacia under varying oxzidation-reduction potential conditions. Water Environ Res 69 1094-1099. 

Riedel A, S Fetzner, M Rampp, F Lingens, U Liebl, J-L Zrmmermann, W Nitschke (1995) EPR, electron spin echo envelope modulation, and electron nuclear double resonance studies of the 2Ee-2S centers of the 2-halobenzoate 1,2-dioxygenase from Burkholderia (Pseudomonas) cepacia 2CBS. J Biol Chem 270 30869-30873. 

As might be expected, bacteria have been isolated from the plants that prodnce flnoroacetate, and these include an unidentified Pseudomonas sp. (Goldman 1965), a strain of Burkholderia Pseudomonas) cepacia from Dichapetalum cymosum (Meyer et al. 1990), and a strain of Morax-ella sp. (Kawasaki et al. 1981). In addition, fluoroacetate is an unusual product of microbial metabolism ... 

Mycobacterium sp. BBl Pseudomonas cepacia F297 Pseudomonas putida GZ44 Mycobacterium sp. RJGll-135 Burkholderia cepacia Pseudomonas paucimobilis Pseudomonas paucimobilis Mycobacterium vanbaalenii PYR-1... 

A two-component 2-halobenzoate 1,2-dioxygenase has been purified from Pseudomonas cepacia strain 2CBS that is able to metabolize 2-fluorobenzoate, 2-chlorobenzoate, 2-bromobenzoate, and 2-iodobenzoate to catechol by concomitant decarboxylation and loss of halide (Fetzner et al. 1992). The inducible 2-halobenzoate 1,2-dioxygenase consisted of... 

Haak B, S Fetzner, F Lingens (1995) Cloning, nucleotide sequence, and expression of the plasmid-encoded genes for the two-component 2-halobenzoate 1,2-dioxygenase from Pseudomonas cepacia 2CBS. J Bacterial Yll 667-675. 

The degradation of 3-chloro-4-methylaniline by Pseudomonas cepacia strain CMAl involved ring fission of 3-chloro-4-methylcatechol by an intradiol enzyme (Stockinger et al. 1992). 

Stockinger J, C Hinteregger, M Loidl, A Ferschl, F Streichsbier (1992) Mineralizarion of 3-chloro-4-methy-lamiline via an orr/jo-cleavage pathway by Pseudomonas cepacia strain CMAl. Appl Microbiol Bio-technol 38 421-428. 

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