STRUCTURE, CHEMOMECHANICAL PROPERTIES AND DEGRADABILITY OF POLYHYDROXYALKANOATES: A REVIEW

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Nuttapol Tanadchangsaeng

Abstract

Interest in biodegradable plastics made from renewable resources has increased significantly in recent years. Bacterially produced polyhydroxyalkanoates (PHAs) are fully biodegradable polyesters which attracted much attention recently as alternative, biodegradable substitutes for petroleum-derived synthetic polymers. PHAs are intracellular energy and carbon storage materials produced by numerous bacteria from biorenewable and biowaste resources. The properties of these biological polyesters are affected by the incorporation of different monomer units in PHA copolymer structure leading to a variety of subsequent superior properties such as biodegradability, biocompatibility, thermoprocessibility. The identification of longer side-chains 3-hydroxyalkanoate (3HA) units other than the most extensively-studied 3-hydroxybutyrate (3HB) unit as constituents of microbial polyesters has an important impact on the structure, physical properties and enzymatic degradabilities of PHA polymer. In this review, the crucial topics concerning with current understanding of PHAs, especially structure, material properties, enzymatic degradation, polymer crystallization and the effect of composition and microstructure structures were described

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Tanadchangsaeng N. STRUCTURE, CHEMOMECHANICAL PROPERTIES AND DEGRADABILITY OF POLYHYDROXYALKANOATES: A REVIEW. Interprof J Health Sci [Internet]. 2023 Oct. 5 [cited 2024 Dec. 6];12(1):9-21. Available from: https://li05.tci-thaijo.org/index.php/IJHS/article/view/89
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References

Abe H, Doi Y. 1999. Structural effects on enzymatic degradabilities for poly[(R)-3-hydroxybutyric acid] and its copolymers. Int. J. Biol. Macromol. 25:185-192.

Abe H, Doi Y, Aoki H, Akehata T. 1998. Solid-state structures and enzymatic degradabilities for melt-crystallized films of copolymers of (R)-3-hydroxybutyric acid with different hydroxyalkanoic acids. Macromolecules 31:1791-1797.

Abe H, Doi Y, Aoki H, Akehata T, Hori Y, Yamaguchi A. 1995a. Physical properties and enzymic degradability of copolymers of (R)-3-hydroxybutyric and 6-hydroxyhexanoic acids. Macromolecules 28:7630-7637.

Abe H, Matsubara I, Doi Y. 1995b. Physical properties and enzymic degradability of polymer blends of bacterial poly[(R)-3-hydroxybutyrate] and poly[(R,S)-3-hydroxybutyrate] stereoisomers. Macromolecules 28:844-853.

Akaraonye E, Keshavarz T, Roy I. 2010. Production of polyhydroxyalkanoates: the future green materials of choice. J. Chem. Tech. Biotechnol. 85(6):732-743.

Anderson, AJ, Dawes EA. 1990. Occurrence, metabolism, metabolic role, and industrial uses of bacterial polyhydroxyalkanoates. Microbiol. Rev. 54:450-472.

Aoyagi Y, Doi Y, Iwata T. 2003. Mechanical properties and highly ordered structure of ultra-high-molecular-weight poly[(R)-3-hydroxybutyrate] films: Effects of annealing and two-step drawing. Polym. Degrad. Stab. 79:209-216.

Ashby RD, Solaiman DKY, Foglia TA. 2005. Synthesis of short-/medium-chain-length poly(hydroxyalkanoate) blends by mixed culture fermentation of glycerol. Biomacromolecules 6(4):2106-2112.

Averous L. 2004. Biodegradable multiphase systems based on plasticized starch: A review. J. Macromol. Sci. Polym. Rev. C44:231-274.

Bachmann BM, Seebach D. 1999. Investigation of the enzymatic cleavage of diastereomeric oligo(3-hydroxybutanoates) containing two to eight HB units. A model for the stereoselectivity of PHB depolymerase from alcaligenes faecalis T1. Macromolecules 32:1777-1784.

Barham, PJ, Barker P, Organ SJ. 1992. Physical properties of poly(hydroxybutyrate) and copolymers of hydroxybutyrate and hydroxyvalerate. FEMS Microbiol. Rev. 103:289-297.

Barham PJ, Keller A. 1986. The relationship between microstructure and mode of fracture in polyhydroxybutyrate. J. Mat. Sci. 24:69-77.

Barham PJ, Keller A, Otun EL, Holmes PA. 1984. Crystallization and morphology of a bacterial thermoplastic: poly-3-hydroxybutyrate. J. Mat. Sci. 19(9):2781-2794.

Barker PA, Mason F, Barham PJ. 1990. Density and crystallinity of poly (3-hydroxybutyrate/3-hydroxyvalerate) copolymers. J. Mat. Sci. 25:1952-1956.

Barnard GN, Sanders JKM. 1989. The poly-β-hydroxybutyrate granule in vivo; a new insight based on NMR spectroscopy of whole cells. J. Biol. Chem. 264:3286-3293.

Bloembergen S, Holden DA, Hamer GK, Bluhm TL, Marchessault RH. 1986. Studies of composition and crystallinity of bacterial poly(hydroxybutyrate-co-hydroxyvalerate). Macromolecules 19:2865-2871.

Bluhm TL, Hamer GK, Marchessault RH, Fyfe CA, Veregin RP. 1986. Isodimorphism in bacterial poly(hydroxybutyrate-co-hydroxyvalerate). Macromolecules 19:2871-2876.

Brucato CL, and Wong SS. 1991. Extracellular poly(3-hydroxybutyrate) depolymerase from Penicillium funiculosum: General characteristics and active site studies. Arch. Biochem. Biophys. 290:497-502.

Chanprateep S. 2010. Current trends in biodegradable polyhydroxyalkanoates. J. Biosci. Bioeng. 110:621-632.

Chen GQ. 2009. A microbial polyhydroxyalkanoates (PHA) based bio- and materials industry. Chem. Soc. Rev. 38:2434-2446.

Chia KH, Ooi TF, Atsuza S, Tsuge T, Sudesh K. 2010. Biosynthesis and characterization of novel polyhydroxyalkanoate polymers with high elastic property by Cupriavidus necator PHB−4 transformant. Polym. Degrad. Stab. 95:2226-2232.

Chowdhury AA. 1963. Poly-hydroxybutyric acid-splitting bacteria and an exoenzyme. Arch. Mikrobiol. 47:167-200.

Cobntbekt J, Mabchessault RH. 1972. Physical properties of poly-hydroxybutyrate: IV. Conformational analysis and crystalline structure. J. Mol. Biol. 71:735-756.

De Koning GJM, and Lemstra PJ. 1993. Crystallization phenomena in bacterial poly[(R)-3-hydroxybutyrate]: 2. Embrittlement and rejuvenation. Polymer 34:4089-4094.

Doi Y. 1990. Microbial Polyesters. VCH Publishers: New York.

Doi Y, Kanesawa Y, Kunioka M, Saito T. 1990. Biodegradation of microbial copolyesters: poly(3-hydroxybutyrate-co-3-hydroxyvalerate) and poly(3-hydroxybutyrate-co-4-hydroxybutyrate). Macromolecules 23:26-31.

Doi Y, Kitamura S, Abe H. 1995. Microbial synthesis and characterization of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate). Macromolecules 28:4822-4828.

Grulke EA, Brandrup J, Immergut EH. 1994 Polymer Handbook, 2 Volumes Set. Prentice Hall, New Jersey.

(2013) vol. 21 page 580–605

Gumel AM, Annuar MSM, Chisti Y. 2013. Recent advances in the production, recovery andapplications of polyhydroxyalkanoates. J. Polym. Env. 21:580–605.

Hisano T, Kasuya K, Tezuka Y, Ishii N, Kobayashi T, Shiraki M, Oroudjev E, Hansma H, Iwata T, Doi Y, Saito T, Miki K. 2006. The crystal structure of polyhydroxybutyrate depolymerase from penicillium funiculosum provides insights into the recognition and degradation of biopolyesters. J. Mol. Biol. 356:993-1004.

Hoffman DJ, Davis GT, Lauritzen JI. 1976. Crystalline and non-crystalline solids. Plenum Press, New York.

Holmes PA. 1988. In Developments in Crystalline Polymers-2. Elsevier: London.

Iwata T, Doi Y, Tanaka T, Akehata T, Shiromo M, Teramachi S. 1997. Enzymatic degradation and adsorption on poly[(R)-3-hydroxybutyrate] single crystals with two types of extracellular PHB depolymerases from comamonas acidovorans YM1609 and alcaligenes faecalis T1. Macromolecules 30:5290-5296.

Jaeger KE, Steinbuchel A, Jendrossek D. 1995. Substrate specificities of bacterial polyhydroxyalkanoate depolymerases and lipases: bacterial lipases hydrolyze poly(omega-hydroxyalkanoates). Appl. Environ. Microbiol. 61(8):3113-3118.

Jendrossek D. 1998. Microbial degradation of polyesters: a review on extracellular poly(hydroxyalkanoic acid) depolymerases. Polym. Degrad. Stab. 59:317-325.

Jendrossek D, Handrick R. 2002. Microbial degradation of polyhydroxyalkanoates. Annu. Rev. Microbiol. 56:403-432.

Jendrossek D, Schirmer A, Schlegel HG. 1996a. Biodegradation of polyhydroxyalkanoic acids. Appl. Microbiol. Biotechnol. 46:451-463.

Kamiya N, Sakurai M, Inoue Y, Chujo R, Doi Y. 1991. Study of cocrystallization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) by solid-state high-resolution carbon-13 NMR spectroscopy and differential scanning calorimetry. Macromolecules 24:2178-2182.

Kasuya K, Inoue Y, Doi Y. 1996. Adsorption kinetics of bacterial PHB depolymerase on the surface of polyhydroxyalkanoate films. Int. J. Biol. Macromol. 19:35-40.

Kasuya K, Inoue Y, Yamada K, Doi Y. 1995. Kinetics of surface hydrolysis of poly[(R)-3-hydroxybutyrate] film by PHB depolymerase from Alcaligenes faecalis T1. Polym. Degrad. Stab. 48:167-174.

Kasuya K, Tezuka Y, Ishii N, Yamagata Y, Shiraki M, Saito T, Hisano T, Iwata T, Doi Y. 2007. Molecular characterization of the poly(3-hydroxybutyrate) depolymerase gene from Penicillium funiculosum. Macromol. Symp. 249-250:540-544.

Kato M, Bao HJ, Kang CK, Fukui T, and Doi Y. 1996. Production of a novel copolyester of 3-hydroxybutyric acid and medium-chain-length 3-hydroxyalkanoic acids by Pseudomonas sp. 61-3 from sugars. Appl. Microbiol. Biotechnol. 45:363-370.

Kikkawa Y, Fujita M, Hiraishi T, Yoshimoto M, Doi Y. 2004. Direct observation of poly(3-hydroxybutyrate) depolymerase adsorbed on polyester thin film by atomic force microscopy. Biomacromolecules 5:1642-1646.

Koning GJM. 1995. Physical properties of bacterial poly((R)-3-hydroxyalkanoates). Can. J. Microbiol. 41:303-310.

Koyama N, Doi Y. 1997. Effects of solid-state structures on the enzymatic degradability of bacterial poly(hydroxyalkanoic acids). Macromolecules 30:826-832.

Kunioka M, Tamaki A, Doi Y. 1989. Crystalline and thermal properties of bacterial copolyesters: poly(3-hydroxybutyrate-co-3-hydroxyvalerate) and poly(3-hydroxybutyrate-co-4-hydroxybutyrate). Macromolecules 22:694-697.

Lau NS, Chee JY, Tsuge T, Sudesh K. 2010. Biosynthesis and mobilization of a novel polyhydroxyalkanoate containing 3-hydroxy-4-methylvalerate monomer produced by Burkholderia sp. USM (JCM15050). Biores. Technol. 101:7916-7923.

Lau NS, Tsuge T, Sudesh K. 2011. Formation of new polyhydroxyalkanoate containing 3-hydroxy-4-methylvalerate monomer in Burkholderia sp. Appl. Microbiol. Biotechnol. 89:1599-1609.

Laycock B, Halley P, Pratt S, Werker A, Lant P. 2013. The chemomechanical properties of microbial polyhydroxyalkanoates. Prog. Polym. Sci. 38:536-583.

Lenz RW, Marchessault RH. 2004. Bacterial polyesters: Biosynthesis, biodegradable plastics and biotechnology. Biomacromolecules 6(1):1-8.

Luzier WD. 1992. Materials derived from biomass/biodegradable materials. PNAS 89:839-842.

Sanchez-Cuesta M, Barker PA, Barham PJ. 1992. Cocrystallization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate). J. Mater. Sci. 27:5335-5338.

Yokouchi M, Tadokoro H, Tani H. 1974. Structural studies of polyesters. VII. Molecular and crystal structures of racemic poly(β-ethyl-β-propiolactone). Polym. J. 16:248-255.

Madison LL, Huisman GW. 1999. Metabolic engineering of poly(3-hydroxyalkanoates): From DNA to plastic. Microlbiol. Mol. Biol. Rev. 63:21-53.

Madkour MH, Heinrich D, Alghamdi MA, Shabbaj II, Steinbüchel A. 2013. PHA Recovery from Biomass Biomacromolecules 2013, 14(9):2963-2972.

Matsusaki H, Abe H, Doi Y. 2000. Biosynthesis and properties of poly(3-hydroxybutyrate-co-3-hydroxyalkanoates) by recombinant strains of Pseudomonas sp. 61-3. Biomacromolecules 1:17-22.

Miyazaki S, Takahashi K, Shiraki M, Saito T, Tezuka Y, Kasuya K. 2000. Properties of a poly(3-hydroxybutyrate) depolymerase from Penicillium funiculosum. J. Polym. Environ. 8:175-182.

Mukai K, Yamada K, Doi Y. 1993. Kinetics and mechanism of heterogeneous hydrolysis of poly[(R)-3-hydroxybutyrate] film by PHA depolymerases. Int. J. Biol. Macromol. 15:361-366.

Murase T, Suzuki Y, Doi Y, Iwata T. 2002. Nonhydrolytic fragmentation of a poly[(R)-3-hydroxybutyrate] single crystal revealed by use of a mutant of polyhydroxybutyrate depolymerase. Biomacromolecules 3:312-317.

Nakamura S, Doi Y, Scandola M. 1992. Microbial synthesis and characterization of poly(3-hydroxybutyrate-co-4-hydroxybutyrate). Macromolecules 25:4237-4241.

Nojiri M, Saito T. 1997. Structure and function of poly(3-hydroxybutyrate) depolymerase from Alcaligenes faecalis T1. J. Bacteriol. 179:6965-6970.

Numata K, Abe H, Iwata T. 2009. Biodegradability of poly(hydroxyalkanoate). Materials 2:1104-1126.

Numata K, Sato S, Fujita M, Tsuge T, Iwata T, Doi Y, et al. 2007a. Adsorption effects of poly(hydroxybutyric acid) depolymerase on chain-folding surface of polyester single crystals revealed by mutant enzyme and frictional force microscopy. Polym. Degrad. Stab. 92:176-183.

Numata K, Yamashita K, Fujita M, Tsuge T, Kasuya K, Iwata T, et al. 2007b. Adsorption and hydrolysis reactions of poly(hydroxybutyric acid) depolymerases secreted from Ralstonia pickettii T1 and Penicillium funiculosum onto poly[(R)-3-hydroxybutyric acid]. Biomacromolecules 8:2276-2281.

Numata K, Kikkawa Y, Tsuge T, Iwata T, Doi Y, Abe H. 2006. Adsorption of biopolyester depolymerase on silicon wafer and poly[3-hydroxybutyric acid] single crystal revealed by real-time AFM. Macromol. Biosci. 6:41-50.

Okamura K, Marchessault RH. 1967. Conformation of Biopolymers. Vol. 2. G.N. Ramachandran, Ed, editor. Academic Press, New York. 709.

Orts WJ, Marchessault RH, Bluhm TL. 1991. Thermodynamics of the melting point depression in poly(hydroxybutyrate-co-hydroxyvalerate) copolymers. Macromolecules 24:6435-6438.

Pizzoli M, Scandola M, Ceccorulli G. 1994. Crystallization kinetics and morphology of poly(3-hydroxybutyrate)/cellulose ester blends. Macromolecules 27:4755-4761.

Saito Y, Nakamura S, Hiramitsu M, Doi Y. 1996. Microbial synthesis and properties of poly(3-hydroxybutyrate-co-4-hydroxybutyrate). Int. J. Biol. Macromol. 39:169-174.

Scandola M, Ceccorulli G, Pizzoli M, and Gazzano M. 1992. Study of the crystal phase and crystallization rate of bacterial poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Macromolecules 25:1405-1410.

Scandola M, Focarete ML, Frisoni G. 1998. Simple kinetic model for the heterogeneous enzymatic hydrolysis of natural poly(3-hydroxybutyrate). Macromolecules 31:3846-3851.

Shimamura E, Kasuya K, Kobayashi G, Shiotani T, Shima Y, Doi Y. 1994a. Physical properties and biodegradability of microbial poly(3-hydroxybutyrate-co-3-hydroxyhexanoate). Macromolecules 27:878-880.

Shimamura E, Scandola M, Doi Y. 1994b. Microbial synthesis and characterization of poly(3-hydroxybutyrate-co-3-hydroxypropionate). Macromolecules 27:4429-4435.

Sudesh K, Abe H, Doi Y. 2000. Synthesis, structure and properties of polyhydroxyalkanoates: biological polyesters. Prog. Polym. Sci. 25:1503-1555.

Suyama T, Tokiwa Y, Ouichanpagdee P, Kanagawa T, Kamagata Y. 1998. Phylogenetic affiliation of soil bacteria that degrade aliphatic polyesters available commercially as biodegradable plastics. Appl. Environ. Microbiol. 64:5008-5011.

Tanadchangsaeng N, Kitagawa A, Yamamoto T, Abe H, Tsuge T. 2009. Identification, biosynthesis, and characterization of polyhydroxyalkanoate copolymer consisting of 3-hydroxybutyrate and 3-hydroxy-4-methylvalerate. Biomacromolecules 10(10):2866-2874.

Tokiwa Y, Calabia B, Ugwu C, Aiba S. 2009. Biodegradability of plastics. Materials 10:3722-3742.

Tomasi G, Scandola M, Briese BH, Jendrossek D. 1996. Enzymatic degradation of bacterial poly(3-hydroxybutyrate) by a depolymerase from Pseudomonas lemoignei. Macromolecules 29:507-513.

Van der Hart DL, Orts WJ, and Marchessault RH. 1995. 13C NMR determination of the degree of cocrystallization in random copolymers of poly(hydroxybutyrate-co-hydroxyvalerate). Macromolecules 28:6394-6400.

Witholt B, Kessler B. 1999. Perspectives of medium chain length poly(hydroxyalkanoates), a versatile set of bacterial bioplastics. Curr. Opin. Biotechnol. 10:279-285.

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 (hydroxybutyrate). Polymer 14:267-272.

Yoshie N, Sakurai M, Inoue Y, Chujo R. 1992. Cocrystallization of isothermally crystallized poly(3-hydroxybutyrate-co-3-hydroxyvalerate). Macromolecules 25:2046-2048.