Biosynthesis and biotechnological production of degradable polyhydroxyalkanoic acid

Biotechnology and Bioprocess Engineering

Volumn 2, Issue 1, 1997, Pages 1-10

  Lee, Eun Yeol ^b   Choi, Cha Yong ^a  

^a Seoul National University   (South Korea)

^b Korea Research Institute of Chemical Technology   (South Korea)

Author keywords

Biodegradable plastic; Biosynthetic mechanics; Biotechnological production; Microbial polyester; Polyhydroxyalkanoic acid

Indexed keywords

EID: 53249086011     PISSN: 12268372     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02932454     Document Type: Review

References (77)

1. Anderson, A. J. and E. A. Dawes (1990) Occurrence, metabolism, metabolic role and industrial uses of bacterial polyhydroxyalkanoates. Microbiol. Rev. 54: 450-472.
2. Doi, Y. (1990) Microbial polyesters. VCH. New York.
3. Masamune, S., C. T. Walsh, A. J. Sinskey, and O. P. Peoples (1989) Poly-(R)-3-hydroxybutyrate (PHB) biosynthesis: mechanistic studies on the biological Claisen condensation catalyzed by β-ketoacyl thiolase. Pure & Appl. Chem. 61: 303-312.
4. Holmes, P. A. (1985) Applications of PHB- a microbially produced biodegradable thermoplastic. Phys. Technol. 16: 32-36.
5. Byrom, D. (1987) Polymer synthesis by microorganisms: technology and economics. TIBTECH. 5: 246-250.
6. Byrom, D. (1992) Production of poly-β-hydroxybutyrate: poly-β-hydroxyvalerate copolymers. FEMS Microbiol. Rev. 103: 247-250.
7. Lemoigne, M. (1926) Produits de deshydration et de polymerisation de Pacide β-oxybutyric. Bull. Soc. Chim. Biol. 8: 576-579.
8. Davis, J. B. (1964) Cellular lipids of a Norcardia grown on propane and n-butane. Appl. Microbiol. 12: 301-304.
9. Wallen, L. L. and W. K. Rohwedder (1974) Poly-β-hydroxyalkanoate from activated sludge. Environ. Sci. Technol. 8: 576-579.
10. De Smet, M. J., G. Eggink, B. Witholt, J. Kingma, and H. Wynberg (1983) Characterization of intracellular inclusions formed by Pseudonomas oleovorans during growth on octane. J. Bacteriol. 154: 870-878.
11. Steinbüchel, A., and H. E. Valentin (1995) Diversity of bacterial polyhydroxyalkanoic acids. FEMS Microbiol. Letters. 128: 219-228.
12. Brandl, H., R. A. Gross, R. W. Lenz, and R. C. Fuller (1988) Pseudomonas oleovorans as a source of poly(β-hydroxyalkanoates) for potential applications as biodegradable polyesters. Appl. Environ. Microbiol. 54: 1977-1982.
13. Lageveen, R. G., G. W. Huiseman, H. Preusting, P. Ketelaar, G. Eggink, and B. Witholt (1988) 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. 54: 2924-2932.
14. Haywood, G. W., A. J. Anderson, D. F. Ewing, and E. A. Dawes (1990) Accumulation of a polyhydroxyalkanoate containing primarily 3-hydroxydecanoate from simple carbohydrate substrates by Pseudomonas sp. NCIMB 40135. Appl. Environ. Microbiol. 56: 3354-3359.
15. Timm, A. and A. Steinbüchel (1990) Formation of polyesters consisting of medium-chain-length 3-hydroxyalkanoic acids from gluconate by Pseudomonas aeruginosa and other fluorescent pseudomonads. Appl. Environ. Microbiol. 56: 3360-3367.
16. Huijberts, G. N. M., G. Eggink, P. De Waard, G. W. Huisman, and B. Witholt (1992) Pseudomonas putida KT2442 cultivated on glucose accumulates poly(3-hydroxyalkanoates) consisting of saturated and unsaturated monomers. Appl. Environ. Microbiol. 58: 536-544.
17. Lee, E. Y., S. H. Kang., S. H. Oh., A. Steinbüchel, and C.Y. Choi (1994) Biosynthesis of novel polyhydroxyalkanoates by Pseudomonas sp. p. 229-231. In: W. K. Teo et al. (ed.) Better living through innovative biochemical engineering. Continental Press. Singapore.
18. Lee, E. Y., D. Jendrossek, A. Schimer, C. Y. Choi, and A. Steinbüchel (1995) Biosynthesis of copolyesters consisting of 3-hydroxybutyric acid and medium-chain-length 3-hydroxyalkanoic acids from 1,3-butanediol or from 3-hydroxybutyrate by Pseudomonas sp. A33. Appl. Microbiol. Biotechnol. 42: 901-909.
19. Lee, E. Y. and C. Y. Choi (1995) Gas chromatography-mass spectrometric analysis and its application to a screening procedure for novel bacterial polyhydroxyalkanoic acids containing long chain saturated and unsaturated monomers. J. Ferment. Bioeng. 80: 408-414.
20. Eggink, G., P. de Waard, and G. N. M. Huijberts (1990) Production of poly-3-hydroxyalkanoates by P. putida during growth on long-chain fatty acids. p.441-444. In: E. A. Dawes (ed.) Novel biodegradable microbial polymers. Kluwer Academic Publishers. Dordrecht, Netherlands.
21. Doi, Y., M. Kunioka, Y. Nakamura, and K. Soga (1988) Nuclear magnetic resonance studies on unusual bacterial copolyesters of 3-hydroxybutyrate and 4-hydroxybutyrate. Macromol. 21: 2722-2727.
22. Doi, Y., A. Tamaki, M. Kunioka, and K. Soga (1987) Biosynthesis of terpolyesters of 3-hydroxybutyrate, 3-hydroxyvalerate, and 5-hydroxyvalerate in Alcaligenes eutrophus from 5-chloropentanoic and pentanoic acids. Makromol. Chem. Rapid Commun. 8: 631-635.
23. Kunioka, M., Y. Nakamura, and Y. Doi (1988) New bacterial copolyesters produced in Alcali-genes eutrophus from organic acids. Polymer Commun. 29: 174-176.
24. Valentin, H. E., A. Schönebaum, and A. Steinbüchel (1992) Identification of 4-hydroxyvaleric acid as a constituent of biosynthetic polyhydroxyalkanoic acids from bacteria. Appl. Microbiol. Biotechnol. 36: 507-514.
25. Valentin, H. E., E. Y. Lee, C. Y. Choi, and A. Steinbüchel (1994) Identification of 4-hydroxyhexanoic acid as a new constituent of biosynthetic polyhydroxyalkanoic acids from bacteria. Appl. Microbiol. Biotechnol. 40: 710-716.
26. Lee, E. Y. and C. Y. Choi (1997) Structural identification of polyhydroxyalkanoic acid (PHA) containing 4-hydroxyalkanoic acids by gas chromatography-mass spectrometry (GC-MS) and its application to bacteria screening. Biotech. Techniques. 11: 167-171.
27. Fritzsche, K., R. W. Lenz, and R. C. Fuller (1990) An unusual bacterial polyester with a phenyl pendent group. Macromol. Chem. 191: 1957-1965.
28. Fritzsche, K., R. W. Lenz, and R. C. Fuller (1990) Bacterial polyesters containing branched poly(β-hydroxyalkanoate) units. Int. J. Biol. Macromol. 12: 92-101.
29. Fritzsche, K., R. W. Lenz, and R. C. Fuller (1990) Production of unsaturated polyesters by Pseudomonas oleovorans. Int. J. Biol. Macromol. 12: 85-91.
30. Lenz, R. W., Y. B. Kim, and R. C. Fuller (1992) Production of unusual bacterial polyesters by Pseudomonas oleovorans through cometabolism. FEMS Microbiol. Rev. 103: 207-214.
31. Valentin, H. E. and A. Steinbüchel (1994) Application of enzymatically synthesized short-chain-length hydroxy fatty acid coenzyme A thioesters for assay of polyhydroxyalkanoic acid synthase. Appl. Microbiol. Biotechnol. 40: 699-709.
32. Dawes, E. A. and P. J. Senior (1973) Energy reserve polymers in microorganisms. Arch. Microbiol. Physiol. 14: 203-266.
33. Reusch, R. N. and H. L. Sadoff (1988) Putative structure and functions of a poly-β-hydroxybutyrate/calcium polyphosphate channel in bacterial plasma membranes. Proc. Natl. Sci. USA. 85: 4176-4180.
34. Barnard, G. N. and K. M. Sanders (1989) The poly-β-hydroxybutyrate granule in vivo. J. Biol. Chem. 24: 3286-3291
35. Gerngross, T. U., P. Reilly, J. Stubbe, A. J. Sinskey, and O. P. Peoples (1993) Immunocytochemical analysis of poly-β-hydroxybutyrate (PHB) synthase in Alcaligenes eutrophus H16: Localization of the synthase enzyme at the surface of PHB granules. J. Bacteriol. 175: 5289-5293.
36. Lauzier, C., J. -F. Revol, and R. H. Marchessault (1992) Topotactic crystallization of isolated poly (P-hydroxybutyrate) granules from Alcaligenes eutrophus. FEMS Microbiol. Rev. 103: 299-310.
37. Shirakura, Y., T. Fukui, T. Saito, Y. Okamoto, T. Narikawa, K. Koide, K. Tomita, T. Takemasa, and S. Masamune (1986) Degradation of poly(3- hydroxybutyrate) by poly(3-hydroxybutyrate) depolymerase from Alcaligenes eutrophus T1, Biochim. Biophys. Acta. 880: 46-53.
38. Schimer, A., D. Jendrossek, and H. G. Schlegel (1993) Degradation of poly(3-hydroxyoctanoic acid)[P(3HO)] by bacteria: purification and properties of a P(3HO) depolymerase from Pseudomonas fluorescens GK13. Appl. Environ. Microbiol. 59: 1220-1227.
39. Gerngross, T. U., P. Reilly, J. Stubbe, A. J. Sinskey, and O. P. Peoples (1993) Immunocytochemical analysis of poly-β-hydroxybutyrate (PHB) synthase in Alcaligenes eutrophus H16: Localization of the synthase enzyme at the surface of PHB granules. J. Bacteriol. 175: 5289-5293.
40. Haywood, G. W., A. J. Anderson, and E. A. Dawes (1988) Characterization of two 3-ketothiolases possessing differing substrate specificities in the polyhydroxyalkanoate synthesizing organism Alcaligenes eutrophus. FEMS Microbiol. Lett. 52: 91-96.
41. Steinbüchel, A. and H. G. Schlegel (1991) Physiology and molecular genetics of poly(β-hydroxyalkanoic acid) synthesis in Alcaligenes eutrophus, Molecular Microbiol. 5: 535-542.
42. Haywood, G. W., A. J. Anderson, L. Chu, and E. A. Dawes (1988) The role of NADH- and NADPH-linked acetoacetyl-CoA reductases in the poly-3- hydroxybutyrate synthesizing organism Alcaligenes eutrophus. FEMS Microbiol. Lett. 52: 259-264.
43. Haywood, G. W., A. J. Anderson, L. Chu, and E. A. Dawes (1989) The importance of PHB-synthase substrate specificity in polyhydroxyalkanoate synthesis by Alcaligenes eutrophus. FEMS Microbiol. Lett. 57: 1-6.
44. Slater, S., T. Gallaher and, D. Dennis (1992) Production of poly (3-hydroxybutyrate-co-3-hydroxyvalerate) in a recombinant Escherichia coli strain. Appl. Environ. Microbiol. 58: 1089-1094.
45. Schubert, P., A. Steinbüchel, and H. G. Schlegel (1988) Cloning of the Alcaligenes eutrophus genes for synthesis of poly-β-hydroxybutyric acid (PHB) and synthesis of PHB in Escherichia coli. J. Bacteriol. 170: 5837-5847.
46. Peoples, O. P. and A. J. Sinskey (1989) Poly-β-hydroxybutyrate (PHB) biosynthesis in Alcaligenes eutrophus H16: Characterization of the genes encoding β-ketothiolase and acetoacetyl-CoA reductase. J. Biol. Chem. 264: 15293-15297.
47. Peoples, O. P. and A. J. Sinskey (1989) Poly-β-hydroxybutyrate (PHB) biosynthesis in Alcaligenes eutrophus H16: Identification and characterization of the PHB polymerase gene (phbC). J. Biol. Chem. 264: 15298-15303.
48. Schubert, P., N. Kruger, and A. Steinbüchel (1991) Molecular analysis of the Alcaligenes eutrophus poly(3-hydroxybutyrate) [PHB] biosynthetic operon: identification of the N-terminus of PHB synthase and identification of the promoter. J. Bacteriol. 173: 168-175.
49. Steinbüchel, A., E. Hustede, M. Liebergesell, U. Pieper, A. Timm, and H. Valentin (1992) Molecular basis for biosynthesis and accumulation of polyhydroxyalkanoic acids in bacteria. FEMS Microbiol. Rev. 103: 217-230.
50. Huisman, G. W., E. Wonink, R. Meima, B. Katzeimer, P. Terpstre, and B. Witholt (1991) Metabolism of poly(3-hydroxyalkanoates) by Pseudomonas oleovorans: identification and sequences of genes and function of the encoded proteins in the synthesis and degradation of PHA. J. Biol. Chem. 266: 2191-2198.
51. Timm, A. and A. Steinbüchel (1992) Cloning and molecular analysis of the poly(3-hydroxyalkanoic acid) gene locus of Pseudomonas aeruginosa PAO 1. Eur. J. Biochem. 209: 15-30.
52. Timm, A., S. Wiese, and A. Steinbüchel (1994) A general method for identification of polyhydroxyalkanoic acid genes from pseudomonads belonging to the rRNA homology group I. Appl. Microbiol. Biotechnol. 40: 669-675.
53. Liebergesell, M., F. Mayer, and A. Steinbüchel (1993) Analysis of polyhydroxyalkanoic acid-biosynthesis genes of anoxygenic phototrophic bacteria reveals synthesis of a polyester exhibiting an unusual composition. Appl. Microbiol. Biotechnol. 40: 292-300.
54. Haywood, G. W., A. J. Anderson, D. R. Williams, and E. A. Dawes (1991) Accumulation of a poly (hydroxyalkanoate) copolymer containing primarily 3-hydroxyvalerate from simple carbohydrate substrates by Rhodococcus sp. NCIMB 40126. Int. J. Biol. Macromol. 13: 83-88.
55. Lee, E. Y. (1995) Microbial Synthesis and Genetic Engineering for Production of Novel Biodegradable Polyhydroxyalkanoates. Seoul National University, Seoul, Korea.
56. Schulz, H. and W. H. Kunau (1987) Beta-oxidation of unsaturated fatty acids: a revised pathway. TIBS. 12: 403-406.
57. Lee, E. Y., W. J. Choi, A. Steinbüchel, and C. Y. Choi (1996) Cell-recycle fed-batch production of a highly unsaturated polyhydroxyalkanoate from 1, 3-butanediol by Pseudomonas sp. A33, J. Environ. Polym. Degrad. 4: 103-112.
58. Anderson, A. J., D. R. Williams, B. Taidi, E. A. Dawes, and D. F. Ewing (1992) Studies on copolyester synthesis by Rhodococcus ruber and factors influencing the molecular mass of polyhydroxybutyrate accumulated by Methylobacterium extorquens and Alcaligenes eutrophus. FEMS Microbiol. Rev. 103: 93-102.
59. Steinbüchel, A. and U. Pieper (1992) Production of a copolyester of 3-hydroxybutyric acid and 3-hydroxyvaleric acid from single unrelated carbon sources by a mutant of Alcaligenes eutrophus. Appl. Microbiol. Biotechnol. 37: 1-6.
60. Lee, E. Y., S. H. Kang, and C.Y. Choi (1995) Biosynthesis of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) by newly isolated Agrobacterium sp. SH-1 and GW-014 from structurally unrelated carbon substrates. J. Ferment. Bioeng. 79: 328-334.
61. Doi, Y., A. Tamaki, M. Kunioka, and Soga, K. (1987) Biosynthesis of an unusual copolyester (10 mol% 3-hydroxybutyrate and 90 mol% 3-hydroxyvalerate units) in Alcaligenes eutrophus from pentanoic acids. J. Chem. Soc. Chem. Commun. 21: 1635-1636.
62. Doi, Y., A. Tamaki, M. Kunioka, and K. Soga (1988) Production of copolyesters of 3-hydroxybutyrate and 3-hydroxyvalerate by Alcaligenes eutrophus from butyric and pentanoic acids. Appl. Microbiol. Biotechnol. 28: 330-334.
63. Timm, A., D. Byrom, and A. Steinbüchel (1990) Formation of blends of various poly(3-hydroxyalkanoic acids) by a recombinant strain of Pseudomonas oleovorans. Appl. Microbiol. Biotechnol. 33: 296-301.
64. Prusting, H., J. Kingma, G. Huisman, A. Steinbüchel, and B. Witholt (1992) Formation of polyester blends by a recombinant strain of Pseudomonas oleovorans: different poly(3-hydroxyalkanoates) are stored in separate granules. J. Environ. Polym. Degrad. 1: 11-21.
65. Doi, Y., Y. Kanesawa, M. Kunioka, and T. Saito (1990) Biodegradation of microbiol copolyesters: poly(3-hydroxybutyrate-co-3-hydroxyvalerate) and poly(3-hydroxybutyrate-co-4-hydroxyvalerate). Macromol. 23: 26-31.
66. Inoue, Y. and N. Yoshie (1992) Structure and physical properties of bacterially synthesized polyesters. Prog. Polym. Sci. 17: 571-610.
67. Bluhm, T. L., G. K. Hamer, R. H. Marchessaults, C. A. Fyfe, and R. P. Veregin (1986) Isodimorphism in bacterial poly(P-hydroxybutyrate-co-β- hydroxyvalerate). Macromol. 19: 2871-2876.
68. Helmut, B., R. A. Gross, R. W. Lenz, and R. C. Fuller (1990) Plastics from bacteria and for bacteria: poly(p-hydroxyalkanoates) as natural, biocompatible, and biodegradable polyesters. p.77-93. In: T. K. Ghose et al. (ed.) Advances in biochemical engineering. Springer-Verlag. Berlin.
69. Hrabak, O. (1992) Industrial production of poly-β-hydroxybutyrate. FEMS Microbiol. Rev. 103: 251-256.
70. Lee, S. Y. (1995) Bacterial polyhydroxyalkanoates. Biotechnol. Bioeng. 49: 1-14.
71. Kim, B. S., S. C. Lee, S. Y. Lee, H. N. Chang, Y. K. Chang, and S. I. Woo (1994) Production of poly(3-hydroxybutyric acid) by fed-batch culture of Alcaligenes eutrophus with glucose concentration control. Biotechnol. Bioeng. 43: 892-898.
72. Lee, S. Y., H. N. Chang, and Y. K. Chang (1994) Production of poly(p-hydroxybutyric acid) by recombinant Escherichia coli. Ann. NY Acad. Sci. 721: 43-53.
73. Lee, S. Y., K. S. Yim, H. N. Chang, and Y. K. Chang (1994) Construction of plasmids, estimation of plasmid stability, and use of stable plasmids for the production of poly(3-hydroxybutyric acid) in Escherichia coli. J. Biotechnol. 32: 203-211.
74. Anonymous (1992) Technology and commercial opportunities in biodegradable polymers. Bioinformation Associates. Boston.
75. Poirier, Y., D. Dennis, K. Klomparene, and C. Somerville (1992) Polyhydroxybutyrate, a biodegradable thermoplastic, produced in transgenic plants. Science 256: 520-523.
76. Poirier, Y., D. Dennis, K. Klomparene, C. Nawrath, and C. Somerville (1992) Perspectives on the production of polyhydroxyalkanoates in plants. FEMS Microbiol. Rev. 103: 237-246.
77. Poirier, Y., C. Nawrath, and C. Somerville (1995) Production of polyhydroxyalkanoates, a family of biodegradable plastics and elastomers, in bacteria and plants. Bio/technology 13: 142-150.