An unusual bacterial polyester with a phenyl pendant group

Fritzsche, Katharina; Lenz, Robert W.; Fuller, R. C.

doi:10.1002/macp.1990.021910821

Cited by 135 publications

(84 citation statements)

References 7 publications

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“…At the same C-3 or β position, an alkyl group which can vary from methyl to tridecyl is positioned ( Figure 1). However, this alkyl side chain is not necessarily saturated: aromatic, unsaturated, halogenated, epoxidized and branched monomers have been reported as well (51)(52)(53)(54)(55). The majority of PHAs are composed of R(-)-3-hydroxyalkanoic acid monomers ranging from C 3 to C 14 carbon atoms with a variety of saturated or unsaturated and straight or branched chain containing aliphatic or aromatic side groups (27,56).…”

Section: Chemical Structurementioning

confidence: 99%

Bacterial polyhydroxyalkanoates-eco-friendly next generation plastic: Production, biocompatibility, biodegradation, physical properties and applications

Muhammadi

Shabina

Afzal

et al. 2015

Green Chemistry Letters and Reviews

266

139

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Polyhydroxyalkanoates (PHAs) are intracellular aliphatic polyesters synthesized as energy reserves, in the form of water-insoluble, nano-sized discrete and optically dense granules in cytoplasm by a diverse bacteria and some archae under conditions of limiting nutrients in the presence of excess carbon source. Bacteria synthesize different PHAs from coenzyme A thioesters of respective hydroxyalkanoic acid, and degrade intracellularly for reuse and extracellularly in natural environments by other microorganisms. In vivo, PHAs exist as amorphous mobile liquid and water-insoluble inclusions but in vitro, exhibit material and mechanical properties, ranging from stiff and brittle crystalline to elastomeric and molding, similar to petrochemical thermoplastics. Further, they are hydrophobic, isotactic, biocompatible and exhibit piezoelectric properties. But as commodity plastics their applications are limited by high production cost, low yield, in vivo degradation, complexity of technology and difficulty of extraction. Therefore, to replace the conventional plastic with PHAs, it is prerequisite to standardize the PHA production systems.

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Section: Chemical Structurementioning

confidence: 99%

Bacterial polyhydroxyalkanoates-eco-friendly next generation plastic: Production, biocompatibility, biodegradation, physical properties and applications

Muhammadi

Shabina

Afzal

et al. 2015

Green Chemistry Letters and Reviews

266

139

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“…For these experiments, cells grown in a chemically defined medium (MM) (54) containing different concentrations of n-phenylalkanoic acids as the sole carbon sources (see above) were used. The contents and composition of PHPhAs were determined by gas chromatography as previously reported (49).…”

Section: Methodsmentioning

confidence: 99%

Novel Biodegradable Aromatic Plastics from a Bacterial Source

García

Olivera

Miñambres

et al. 1999

Journal of Biological Chemistry

120

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Novel biodegradable bacterial plastics, made up of units of 3-hydroxy-n-phenylalkanoic acids, are accumulated intracellularly by Pseudomonas putida U due to the existence in this bacterium of (i) an acyl-CoA synthetase (encoded by the fadD gene) that activates the aryl-precursors; (ii) a ␤-oxidation pathway that affords 3-OH-aryl-CoAs, and (iii) a polymerization-depolymerization system (encoded in the pha locus) integrated by two polymerases (PhaC1 and PhaC2) and a depolymerase (PhaZ). The complete assimilation of these compounds requires two additional routes that specifically catabolize the phenylacetyl-CoA or the benzoyl-CoA generated from these polyesters through ␤-oxidation. Genetic studies have allowed the cloning, sequencing, and disruption of the genes included in the pha locus (phaC1, phaC2, and phaZ) as well as those related to the biosynthesis of precursors (fadD) or to the catabolism of their derivatives (acuA, fadA, and paa genes). Additional experiments showed that the blockade of either fadD or phaC1 hindered the synthesis and accumulation of plastic polymers. Disruption of phaC2 reduced the quantity of stored polymers by two-thirds. The blockade of phaZ hampered the mobilization of the polymer and decreased its production. Mutations in the paa genes, encoding the phenylacetic acid catabolic enzymes, did not affect the synthesis or catabolism of polymers containing either 3-hydroxyaliphatic acids or 3-hydroxy-nphenylalkanoic acids with an odd number of carbon atoms as monomers, whereas the production of polyesters containing units of 3-hydroxy-n-phenylalkanoic acids with an even number of carbon atoms was greatly reduced in these bacteria. Yield-improving studies revealed that mutants defective in the glyoxylic acid cycle (isocitrate lyase ؊ ) or in the ␤-oxidation pathway (fadA), stored a higher amount of plastic polymers (1.4-and 2-fold, respectively), suggesting that genetic manipulation of these pathways could be useful for isolating overproducer strains. The analysis of the organization and function of the pha locus and its relationship with the core of the phenylacetyl-CoA catabolon is reported and discussed.

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“…To our knowledge, this is the first report on the formation of waxes and TAGs containing aromatic constituents in bacteria. In this context, the accumulation of unusual polyhydroxyalkanoates bearing a phenyl group by Pseudomonas species has to be mentioned (Fritzsche et al, 1990 ;Garcı! a et al, 1999).…”

Section: Discussionmentioning

confidence: 99%

Identification of phenyldecanoic acid as a constituent of triacylglycerols and wax ester produced by Rhodococcus opacus PD630

et al. 2002

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Phenyldecane supported growth and lipid accumulation of Rhodococcus opacus PD630 during cultivation under nitrogen-limiting conditions. The results of this study suggested that the hydrocarbon phenyldecane was degraded by monoterminal oxidation, followed by β-oxidation of the alkyl side-chain to phenylacetic acid, and by an additional degradative route for the oxidation of the latter to intermediates of the central metabolism. α-Oxidation of phenyldecanoic acid also occurred to some extent. Phenyldecanoic acid, the monoterminal oxidation product, was also utilized for the biosynthesis of a novel wax ester and novel triacylglycerols. The formation of the wax ester phenyldecylphenyldecanoate probably resulted from the condensation of phenyldecanoic acid and phenyldecanol, which were produced as metabolites during the catabolism of phenyldecane. Two types of triacylglycerol were detected in phenyldecane-grown cells of strain PD630. Triacylglycerols containing only odd-and even-numbered aliphatic fatty acids, as well as triacylglycerols in which one fatty acid was replaced by a phenyldecanoic acid residue, occurred. Other phenyl intermediates, such as phenylacetic acid, phenylpropionic acid, 4-hydroxyphenylpropionic acid, protocatechuate and homogentisic acid, were excreted into the medium during cultivation on phenyldecane. On the basis of the results obtained, pathways for the catabolism and assimilation of phenyldecane by R. opacus PD630 are discussed.

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An unusual bacterial polyester with a phenyl pendant group

Cited by 135 publications

References 7 publications

Bacterial polyhydroxyalkanoates-eco-friendly next generation plastic: Production, biocompatibility, biodegradation, physical properties and applications

Bacterial polyhydroxyalkanoates-eco-friendly next generation plastic: Production, biocompatibility, biodegradation, physical properties and applications

Novel Biodegradable Aromatic Plastics from a Bacterial Source

Identification of phenyldecanoic acid as a constituent of triacylglycerols and wax ester produced by Rhodococcus opacus PD630

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