Abstract
Two types of novel aromatic copolyesters were synthesized from 11-phenoxyundecanoic acid (11-POU) as the sole carbon source and the cosubstrates 11-POU and octanoate, respectively, by isolated Pseudomonas putida BM01 that is known to accumulate high concentrations of medium-chain-length polyesters. Insoluble 11-POU was recrystallized in situ in buffer by alkaline treatment and pH adjustment, followed by autoclaving. The resulting microcrystals, whose structure was different from that of the commercially available crystalline powder, suspended in media were rapidly consumed by the bacterium. Synthesized polymers were characterized by gas chromatography, nuclear magnetic resonance spectroscopy, and differential scanning calorimetry. The aromatic copolyesters synthesized from 11-POU were composed of two monomer units consisting of 3-hydroxy-5-phenoxyvalerate (5POHV) as the major component (72 to 85 mol%) and 3-hydroxy-7-phenoxyheptanoate (7POHH) as the minor component (15 to 28 mol%). The aromatic copolyesters showed a crystalline melting transition at 70(deg)C. When the bacterium was grown on the cosubstrates 11-POU and octanoate, the bacterium synthesized the copolyesters composed of aromatic and aliphatic monomers poly(5POHV-co-7POHH-co-3-hydroxy-9-phenoxynonanoate-co-3-hydroxyalkanoates) . The addition of octanoate in the feed shifted the major monomer unit in the polymer from 5POHV to 7POHH. A further-fragmented metabolite, 3-phenoxypropionate, whose concentration reached a steady state at the time of greatest polyester accumulation, was detected in the medium. The metabolic pathway of 11-POU is suggested.
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- Choi M. H., Yoon S. C. Polyester Biosynthesis Characteristics of Pseudomonas citronellolis Grown on Various Carbon Sources, Including 3-Methyl-Branched Substrates. Appl Environ Microbiol. 1994 Sep;60(9):3245–3254. doi: 10.1128/aem.60.9.3245-3254.1994. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Fritzsche K., Lenz R. W., Fuller R. C. Bacterial polyesters containing branched poly(beta-hydroxyalkanoate) units. Int J Biol Macromol. 1990 Apr;12(2):92–101. doi: 10.1016/0141-8130(90)90059-j. [DOI] [PubMed] [Google Scholar]
- Fritzsche K., Lenz R. W., Fuller R. C. Production of unsaturated polyesters by Pseudomonas oleovorans. Int J Biol Macromol. 1990 Apr;12(2):85–91. doi: 10.1016/0141-8130(90)90058-i. [DOI] [PubMed] [Google Scholar]
- Huijberts G. N., Eggink G., de Waard P., Huisman G. W., Witholt B. Pseudomonas putida KT2442 cultivated on glucose accumulates poly(3-hydroxyalkanoates) consisting of saturated and unsaturated monomers. Appl Environ Microbiol. 1992 Feb;58(2):536–544. doi: 10.1128/aem.58.2.536-544.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Lageveen R. G., Huisman G. W., Preusting H., Ketelaar P., Eggink G., Witholt B. Formation of Polyesters by Pseudomonas oleovorans: Effect of Substrates on Formation and Composition of Poly-(R)-3-Hydroxyalkanoates and Poly-(R)-3-Hydroxyalkenoates. Appl Environ Microbiol. 1988 Dec;54(12):2924–2932. doi: 10.1128/aem.54.12.2924-2932.1988. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Warhurst A. M., Fewson C. A. Microbial metabolism and biotransformations of styrene. J Appl Bacteriol. 1994 Dec;77(6):597–606. doi: 10.1111/j.1365-2672.1994.tb02807.x. [DOI] [PubMed] [Google Scholar]
- de Waard P., van der Wal H., Huijberts G. N., Eggink G. Heteronuclear NMR analysis of unsaturated fatty acids in poly(3-hydroxyalkanoates). Study of beta-oxidation in Pseudomonas putida. J Biol Chem. 1993 Jan 5;268(1):315–319. [PubMed] [Google Scholar]