Polyhydroxyalkanoates (PHAs), Structure, Composition and Solution Properties of
Part 3b. Polyesters
Dr. Naoko Yoshie,
Prof. Yoshio Inoue,
Dr. Naoko Yoshie
- [email protected]
- +81-45-924-5796 | Fax: +81-45-924-5827
Tokyo Institute of Technology, Department of Biomolecular Engineering, Yokohama, Japan, 226-8501
Search for more papers by this authorProf. Yoshio Inoue
- [email protected]
- +81-45-924-5794 | Fax: +81-45-924-5827
Tokyo Institute of Technology, Department of Biomolecular Engineering, Yokohama, Japan, 226-8501
Search for more papers by this authorDr. Naoko Yoshie,
Prof. Yoshio Inoue,
Dr. Naoko Yoshie
- [email protected]
- +81-45-924-5796 | Fax: +81-45-924-5827
Tokyo Institute of Technology, Department of Biomolecular Engineering, Yokohama, Japan, 226-8501
Search for more papers by this authorProf. Yoshio Inoue
- [email protected]
- +81-45-924-5794 | Fax: +81-45-924-5827
Tokyo Institute of Technology, Department of Biomolecular Engineering, Yokohama, Japan, 226-8501
Search for more papers by this authorAbstract
- Introduction
- Historical Outline
- Chemical Structure of PHAs
- Chemical Composition and its Distribution among PHA Copolymers
- Comonomer Composition
- Comonomer Sequence Distribution
- Compositional Fractionation
- Chemical Composition Distribution
- Effect of CCD on Crystalline Structure and Physical Properties
- Crystal Structure of PHAs
- Crystal Structure and Unit Cell Dimensions of Poly(3HA)s
- Isomorphous Behavior of SCL-PHA Copolymers
- Solution Properties of PHAs
- Solvents of PHAs
- Properties in Dilute Solution
- NMR Studies on Solution Properties
References
- Abe, C., Taima, Y., Nakamura, Y., Doi, Y. (1990) New bacterial copolyester of 3-hydroxyalkanoates and 3-hydroxy-ω-fluoroalkanoates produced by Pseudomonasoleovorans, Polymer Commun. 31, 404–406.
- Akita, S., Eigata, Y., Miyaki, Y., Fujita, H. (1976) Solution properties of poly(D-β-hydroxybutyrate). 1.Biosynthesis and characterization, Macromolecules 9, 774–780.
- Aróstegui, S. M., Aponte, M. A., Díaz, E., Schröder, E. (1999) Bacterial polyesters produced by Pseudomonas oleovorans containing nitrophenyl groups, Macromolecules 32, 2889–2895.
- Ballistreri, A., Garozzo, D., Giuffrida, M., Impallomeni, G., Montaudo, G. (1989) Sequencing bacterial poly(β-hydroxybutyrate-co-β-hydroxyvalerate) by partial methanolysis, high-performance liquid chromatography fractionation, and fast atom bombardment mass spectrometry analysis, Macromolecules 22, 2107–2111.
- Ballistreri, A., Montaudo, G., Impallomeni, G., Lenz, R. W., Kim, Y. B., Fuller, C. R. (1990) Sequence distribution of β-hydroxyalkanoate units with higher alkyl groups in bacterial copolyesters, Macromolecules 23, 5059–5064.
- Ballistreri, A., Montaudo, G., Garozzo, D., Giuffrida, M. (1991) Microstructure of bacterial poly(β-hydroxybutyrate-co-β-hydroxyvalerate) by fast atom bombardment mass spectrometry analysis of the partial pyrolysis products, Macromolecules 24, 1231–1236.
- Barham, P. J., Barker, P. A., Organ, S. J. (1992) Physical properties of poly(hydroxybutyrate) and copolymers of hydroxybutyrate and hydroxyvalerate, FEMB Microbiol. Rev. 103, 289–298.
- Barker, P. A., Barham, P. J. (1989) Determination of the composition of bacterially produced poly[(R)-3-hydroxybutyrate/(R)-3-hydroxyvalerate] by polarimetry, J. Mater. Sci. Lett. 8, 1049–1051.
- Barker, P. A., Mason, F., Barham, P. J. (1990) Density and crystallinity of poly(3-hydroxybutyrate/3-hydroxyvalerate) copolymers, J. Mater. Sci. 25, 1952–1956.
- Barker, P. A., Barham, P. J., Martinez-Salazar, J. (1997) Effect of crystallization temperature on the cocrystallization of hydroxybutyrate/hydroxyvalerate copolymers, Polymer 38, 913–919.
- Bloembergen, S., Holden, D. A., Hamer, G. K., Bluhm, T. L., Marchessault, R. H. (1986) Studies of composition and crystallinity of bacterial poly(β-hydroxybutyrate-co-β-hydroxyvalerate), Macromolecules 19, 2865–2871.
- Bluhm, T. L., Hamer, G. K., Marchessault, R. H., Fyfe, C. A., Veregin, R. P. (1986) Isodimorphism in bacterial poly(β-hydroxybutyrate-co-β-hydroxyvalerate), Macromolecules 19, 2871–2876.
- Brandl, H., Gross, R. A., Lenz, R. W., Fuller, R. C. (1988) Pseudomonas oleovorans as a source of poly(β-hydroxyalkanoates) for potential applications as biodegradable polyesters, Appl. Environ. Microbiol. 54, 1977–1982.
- Brandl, H., Knee, E. J., Jr., Fuller, R. C., Gross, R. A., Lenz, R. W. (1989) Ability of the phototrophic bacterium Rhodospirillum rubrum to produce various poly(β-hydroxyalkanoates): potential source for biodegradable polyesters, Int. J. Biol. Macromol. 11, 49–55.
- Cao, A., Ichikawa, M., Kasuya, K., Yoshie, N., Asakawa, N., Inoue, Y., Doi, Y., Abe, H. (1996) Composition fractionation and thermal characterization of poly(3-hydroxybutyrate-co-3-hydroxypropionate), Polym. J. 28, 1096–1102.
- Cao, A., Kasuya, K., Abe, H., Doi, Y., Inoue, Y. (1998) Studies on comonomer compositional distribution of the bacterial poly(3-hydroxybutyric acid-co-3-hydroxypropionic acid)s and crystal and thermal characteristics of their fractionated component copolyesters, Polymer 39, 4801–4816.
- Cao, A., Asakawa, N., Yoshie, N., Inoue, Y. (1999) High-resolution solid-state 13C n.m.r. study on phase structure of the compositionally fractionated bacterial copolyester poly(3-hydroxybutyric acid-co-3-hydroxypropionic acid)s, Polymer 40, 3309–3322.
- Cornibert, J., Marchessault, R. H. (1972) Physical properties of poly-β-hydroxybutyrate IV. Conformational analysis and crystalline structure, J. Mol. Biol. 71, 735–756.
- Cornibert, J., Marchessault, R. H. (1975) Conformational isomorphism. A general 21 helical conformation for poly(β-alkanoates), Macromolecules 8, 296–305.
- Cornibert, J., Marchessault, R. H., Benoit, H., Weill, G. (1970) Physical properties of poly-β-hydroxybutyrate III. Folding of helical segments in 2,2,2-trifluoroethanol, Macromolecules 3, 741–746.
- Dais, P., Nedea, M. E., Morin, F. G., Marchessault, R. H. (1989) 13C spin-lattice relaxation and chain local motions of poly(β-hydroxybutyrate) in tetrachloroethane solution, Macromolecules 22, 4208–4212.
- Dais, P., Nedea, M. E., Morin, F. G., Marchessault, R. H. (1990) Effect of internal librational motions on the carbon-13 nuclear magnetic resonance relaxation times of poly(β-hydroxybutyrate) in tetrachloroethane solution, Macromolecules 23, 3387–3388.
- Doi, Y., Kunioka, M., Nakamura, Y., Soga, K. (1986) Nuclear magnetic resonance studies on poly(β-hydroxybutyrate) and a copolyester of β-hydroxybutyrate and β-hydroxyvalerate isolated from Alcaligenes eutrophus H16, Macromolecules 19, 2860–2864.
- Doi, Y., Tamaki, A., Kunioka, M., Soga, K. (1987) Biosynthesis of terpolyesters of 3-hydroxybutyrate, 3-hydroxyvalerate, and 5-hydroxyvalerate by Alcaligenes eutrophus from 5-chloropentanoic and pentanoic acids, Makromol. Chem. Rapid Commun. 8, 631–635.
- Doi, Y., Tamaki, A., Kunioka, M., Soga, K. (1988a) Production of copolyesters of 3-hydroxybutyrate and 3-hydroxyvalerate by Alcaligenes eutrophus from butyric and pentanoic acids, Appl. Microbiol. Biotechnol. 28, 330–334.
- Doi, Y., Kunioka, M., Nakamura, Y., Soga, K. (1988b) Nuclear magnetic resonance studies on unusual bacterial copolyesters of 3-hydroxybutyrate and 4-hydroxybutyrate, Macromolecules 21, 2722–2727.
- Doi, Y., Kunioka, M., Tamaki, A., Nakamura, Y., Soga, K. (1988c) Nuclear magnetic resonance studies on bacterial copolyesters of 3-hydroxybutyric acid and 3-hydroxyvaleric acid, Makromol. Chem. 189, 1077–1086.
- Doi, Y., Segawa, A., Kunioka, M. (1990) Biosynthesis and characterization of poly(3-hydroxybutyrate-co-4-hydroxybutyrate) in Alcaligenes eutrophus, Int. J. Biol. Macromol. 12, 106–111.
- Fritzsche, K., Lenz, R. W., Fuller, R. C. (1990) Bacterial polyesters containing branched poly(β-hydroxyalkanoate) units, Int. J. Biol. Macromol. 12, 92–101.
- Furuhashi, Y., Iwata, T., Sikorski, P., Atkins, E., Doi, Y. (2000) Structure and morphology of the aliphatic polyester poly-β-propiolactone in solution grown chain-folded lamellar crystals, Macromolecules 33, 9423–9431.
- Goto, Y., Kamiya, N., Yamamoto, Y., Inoue, Y., Chûjô, R., Kunioka, M., Doi, Y. (1989) NMR analysis of microstructure in bacterial poly(3-hydroxybutyrate-co-4-hydroxybutyrate), Rep. Prog. Polym. Phys. Jpn. 32, 639–642.
- Gross, R. A., DeMello, C., Lenz, R. W., Brandl, H., Fuller, R. C. (1989) Biosynthesis and characterization of poly(β-hydroxyalkanoates) produced by Pseudomonas oleovorans, Macromolecules 22, 1106–1115.
- Hiramitsu, M., Doi, Y. (1993) Microbial synthesis and characterization of poly(3-hydroxybutyrate-co-3-hydroxypropionate), Polymer 34, 4782–4786.
- Holmes, P. A. (1985) Applications of PHB – A microbially produced biodegradable thermoplastic, Phys. Technol. 16, 32–36.
- Huglin, M. B., Radwin, M. A. (1991) Unperturbed dimension of poly(β-hydroxybutyrate) in single and binary solvents, Polymer 32, 1293–1298.
- Inoue, Y., Kamiya, N., Yamamoto, Y., Chûjô, R., Doi, Y. (1989) Microstructures of commercially available poly(3-hydroxybutyrate-co-3-hydroxyvalerate)s, Macromolecules 22, 3800–3802.
- Kamiya, N., Yamamoto, Y., Inoue, Y., Chûjô, R., Doi, Y. (1989) Microstructure of bacterially synthesized poly(3-hydroxybutyrate-co-3-hydroxyvalerate, Macromolecules 22, 1676–1682.
- Kamiya, N., Inoue, Y., Yamamoto, Y., Chûjô, R., Doi, Y. (1990) Conformational analysis of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) in solution by 1H NMR spectroscopy, Macromolecules 23, 1313–1317.
- Kamiya, N., Sakurai, M., Inoue, Y., Chûjô, R. (1991a) Isomorphic behavior of random copolymers: thermodynamic analysis of cocrystallization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate), Macromolecules, 24, 3888–3892.
- Kamiya, N., Sakurai, M., Inoue, Y., Chûjô, R., Doi, Y. (1991b) Studies of cocrystallization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) by solid-state high-resolution 13C NMR spectroscopy and differential scanning calorimetry, Macromolecules 24, 2178–2182.
- Kim, Y. B., Lenz, R. W., Fuller, R. C. (1991) Preparation and characterization of poly(β-hydroxyalkanoates) obtained from Pseudomonas oleovorans grown with mixtures of 5-phenylvaleric acid and n-alkanoic acids, Macromolecules 24, 5256–5260.
- Kunioka, M., Nakamura, Y., Doi, Y. (1988) New bacterial copolyesters produced in Alcaligenes eutrophus from organic acids, Polym. Commun. 29, 174–176.
- Kunioka, M., Tamaki, A., Doi, Y. (1989) Crystalline and thermal properties of bacterial copolyesters: poly(3-hydroxybutyrate-co-3-hydroxyvalerate) and (3-hydroxybutyrate-co-4-hydroxybutyrate), Macromolecules 22 694–697.
- Lee, E. Y., Jendrossek, D., Schirmer, A., Choi, C. Y., Steinbüchel, A. (1995) Biosynthesis of copolyesters consisting of 3-hydroxybutyrate and medium-chain-length 3-hydroxyalkanoates from 1,3-butanediol or from 3-hydroxybutyate by Pseudomonas sp. A33, Appl. Microbiol. Biotechnol. 42, 901–909.
- Lee, M.Y., Park, W.H., Lenz, R.W. (2000) Hydrophilic bacterial polyesters modified with pendant hydroxyl groups, Polymer 41, 1703–1709.
- Lemoigne, M. (1926) Produits de deshydration et de polymerisation de l'acide β-oxybutyric, Bull. Soc. Chem. Biol.(Paris) 8, 770–782.
- Marchessault, R. H., Nedea, M. E. (1989) Optical rotatory dispersion of poly(β-hydroxybutyrate-co-β-hydroxyvalerate) for composition determination, Polym. Commun. 30, 261–263.
- Marchessault, R. H., Okamura, K., Su, C. J. (1970) Physical properties of poly-β-hydroxybutyrate II. Conformational aspects in Solution, Macromolecules 3, 735–740.
- Marchessault, R. H., Bluhm, T. L., Deslandes, Y., Hamer, G. K., Orts, W. J., Sundararajan, P. R., Taylor, M. G., Bloembergen, S., Holden, D. A. (1988) Poly(β-hydroxyalkanoates): Biorefinery polymers in search of applications, Makromol. Chem., Macromol. Symp. 19, 235–254.
- Marchessault, R. H., Monasterios, C. J., Morin, F. G., Sundararajan, P. R. (1990) Chiral poly(β-hydroxyalkanoates): an adaptable helix influenced by the alkane side-chain, Int. J. Biol. Macromol. 12, 158–165.
- Mitomo, H., Doi, Y. (1999) Lamellar thickening and cocrystallization of poly(hydroxyalkanoate)s on annealing, Int. J. Biol. Macromol. 25, 201–205.
- Mitomo, H., Morishita, N., Doi, Y. (1993) Composition range of crystal phase transition of isodimorphism in poly(3-hydroxybutyrate-co-3-hydroxyvalerate), Macromolecules 26, 5809–5811.
- Mitomo, H., Takahashi, T., Ito, H., Saito, T. (1999) Biosynthesis and characterization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) produced by Burkholderia cepacia D1, Int. J. Biol. Macromol. 24, 311–318.
- Nakamura, S., Kunioka, M., Doi, Y. (1991) Biosynthesis and characterization of bacterial poly(3-hydroxybutyrate-co-3-hydroxypropionate), Macromol. Rep. A28, 15–24.
- Organ, S.J. (1994) Phase separation in blends of poly(hydroxybutyrate) with poly(hydroxybutyrate-co-hydroxyvalerate): variation with blend components, Polymer 35, 86–92.
- Organ, S.J., Barham, P.J. (1993) Phase separation in a blend of poly(hydroxybutyrate) with poly(hydroxybutyrate-co-hydroxyvalerate), Polymer 34, 459–467.
- Orts, W. J., Marchessault, R. H., Bluhm, T. L. (1991) Thermodynamics of the melting point depression in poly(β-hydroxybutyrate-co-β-hydroxyvalerate) copolymers, Macromolecules 24, 6435–6438.
- Pearce, R. P., Marchessault, R. H., (1994) Melting and crystallization in bacterial poly(β-hydroxyvalerate), PHV and blends with poly(β-hydroxybutyrate-co- hydroxyvalerate), Macromolecules 27, 3869–3874.
- Preusting, H., Nijenhuis, A., Witholt, B. (1990) Physical characteristics of poly(3-hydroxyalkanoates) and poly(3-hydroxyalkenoates) produced by Pseudomonas oleovorans grown on aliphatic hydrocarbons, Macromolecules 23, 4220–4224.
- Saito, M., Inoue, Y., Yoshie, N. (2001) Cocrystallization and phase segregation of blend of poly(3-hydroxybutyrate) and poly(3-hydroxybutyrate-co-3-hydroxyvalerate), Polymer 42, 5573–5580.
- Saito, Y., Doi, Y. (1994) Microbial synthesis and properties of poly(3-hydroxybutyrate-co-4-hydroxybutyrate) in Comamonas acidovorans, Int. J. Biol. Macromol. 16, 99–104.
- Sanchez, I. C., Eby, R. K. (1973) Crystallization of random copolymers, J. Res. Natl. Bur. Stand., Sect. A 77, 353–358.
- Sanchez, I. C., Eby, R. K. (1975) Thermodynamics and crystallization of random copolymers, Macromolecules 8, 638–641.
- Sánchez-Cuesta, M., Martínez-Salazar, J., Barker, P. A., Barham, P. J. (1992) Co-crystallization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate), J. Mater. Sci. 27, 5335–5338.
- Satoh, H., Mino, T., Matsuo, T. (1992) Uptake of organic substrates and accumulation of polyhydroxyalkanoates linked with glycolysis of intracellular carbohydrates under anaerobic conditions in the biological excess phosphate removal process, Wat. Sci. Technol. 26, 933–942.
- Shi, F., Ashby, R. D., Gross, R. A. (1997) Fractionation and characterization of microbial polyesters containing 3-hydroxybutyrate and 4-hydroxybutyrate repeat units, Macromolecules 30, 2521–2523.
- Shiotani, T., Kobayashi, G. (1993) Copolymer and its production, Japanese Pat. Appl. 093049.
- Steinbüchel, A., Valentin, H.E. (1995) Diversity of bacterial polyhydroxyalkanoic acids, FEMS Microbiol. Lett. 128, 219–228.
- Steinbüchel, A., Wiese, S. (1992) A Pseudomonas strain accumulating polyesters of 3-hydroxybutyric acid and medium-chain-length 3-hydroxyalkanoic acids, Appl. Microbiol. Biotechnol. 37, 691–697.
- Steinbüchel, A., Debzi, E. M., Marchessault, R. H., Timm, A. (1993) Synthesis and production of poly(3-hydroxyvaleric acid) homopolyester by Chromobacterium violaceum, Appl. Microbiol. Biotechnol. 39, 443–449.
- Suehiro, K., Chatani, Y., Tadokoro, H. (1975) Structural studies of polyesters. VI. Disordered crystal structure (Form II) of poly(β-propiolactone), Polymer J. 7, 352–358.
- Terada, M., Marchessault, R. H. (1999) Determination of solubility parameters for poly(3-hydroxyalkanoates), Int. J. Biol. Macromol. 25, 207–215.
- Valentin, H. E., Schönebaum, A., Steinbüchel, A. (1992) Identification of 4-hydroxyvaleric acid as a constituent of biosynthetic polyhydroxyalkanoic acids from bacteria, Appl. Microbiol. Biotechnol. 36, 507–514.
- VanderHart, D. L., Orts, W. J., Marchessault, R. H. (1995) 13C NMR determination of the degree of cocrystallization in random copolymers of poly(β-hydroxybutyrate-co-β-hydroxyvalerate), Macromolecules 28, 6394–6400.
- Wasai, T., Saegusa, T., Furukawa, J. (1964) Pori-β-puropiorakuton no bunnshi kouzou (Molecular structure of poly-β-propiolactone), Kougyo Kagaku Zasshi (in Japanese) 67, 601–604.
- Yokouchi, M., Chatani, Y., Tadokoro, H., Teranishi, K., Tani, H. (1973) Structural studies of polyesters: 5. Molecular and crystal structures of optically active and racemic poly(β-hydroxybutyrate), Polymer 14, 267–272.
- Yokouchi, M., Chatani, Y., Tadokoro, H., Tani, H. (1974) Structural studies of polyesters. VII. Molecular and crystal structures of racemic poly(β-ethyl- β-propiolactone), Polym. J. 6, 248–255.
- Yoshie, N., Inoue, Y. (1999) Chemical composition distribution of bacterial copolyesters, Int. J. Biol. Macromol. 25, 193–200.
- Yoshie, N., Sakurai, M., Inoue, Y., Chûjô, R. (1992) Cocrystallization of isothermally crystallized poly(3-hydroxybutyrate-co-3-hydroxyvalerate), Macromolecules 25, 2046–2048.
- Yoshie, N., Menju, H., Sato, H., Inoue, Y. (1995) Complex composition distribution of poly(3-hydroxybutyrate-co-3-hydroxyvalerate), Macromolecules 28, 6516–6521.
- Yoshie, N., Menju, H., Sato, H., Inoue, Y. (1996) Crystallization and melting behavior in blends of poly(3-hydroxybutyrate-co-3-hydroxyvalerate), Polym. J. 28, 45–50.
-
Yoshie, N.,
Fujiwara, M.,
Kasuya, K.,
Abe, H.,
Doi, Y.,
Inoue, Y.
(1999)
Effect of monomer composition and composition distribution on enzymatic degradation of poly(3-hydroxybutyrate-co-3-hydroxyvalerate),
Macromol. Chem. Phys. 200,
977–982.
10.1002/(SICI)1521-3935(19990501)200:5<977::AID-MACP977>3.0.CO;2-Y CAS Web of Science® Google Scholar
Citing Literature
Biopolymers Online: Biology • Chemistry • Biotechnology • Applications
Browse other articles of this reference work:
