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Polyhydroxybutyrate

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(Redirected fromPoly-3-hydroxybutyrate)
Polymer
Polymeric crystals of PHB observed by polarizing optical microscope.

Polyhydroxybutyrate (PHB) is apolyhydroxyalkanoate (PHA), apolymer belonging to thepolyesters class that are of interest as bio-derived andbiodegradable plastics.[1] The poly-3-hydroxybutyrate (P3HB) form of PHB is probably the most common type of polyhydroxyalkanoate, but other polymers of this class are produced by a variety of organisms: these include poly-4-hydroxybutyrate (P4HB), polyhydroxyvalerate (PHV), polyhydroxyhexanoate (PHH), polyhydroxyoctanoate (PHO) and theircopolymers.

Biosynthesis

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PHB is produced bymicroorganisms (such asCupriavidus necator,Methylobacterium rhodesianum orBacillus megaterium) apparently in response to conditions of physiological stress;[2] mainly conditions in which nutrients are limited. The polymer is primarily a product ofcarbon assimilation (fromglucose orstarch) and is employed by microorganisms as a form of energy storage molecule to be metabolized when other common energy sources are not available.[citation needed]

Microbial biosynthesis of PHB starts with thecondensation of two molecules ofacetyl-CoA to give acetoacetyl-CoA which is subsequently reduced to hydroxybutyryl-CoA. This latter compound is then used as a monomer to polymerize PHB.[3] PHAs granules are then recovered by disrupting the cells.[4]

Structure of poly-(R)-3-hydroxybutyrate (P3HB), apolyhydroxyalkanoate
Chemical structures of P3HB, PHV and their copolymer PHBV

Thermoplastic polymer

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Most commercial plastics are synthetic polymers derived frompetrochemicals. They tend to resistbiodegradation. PHB-derived plastics are attractive because they arecompostable and derived from renewables and are bio-degradable.

ICI had developed the material topilot plant stage in the 1980s, but interest faded when it became clear that the cost of material was too high, and its properties could not match those ofpolypropylene. Some bottles were made for Wella's "Sanara" range of shampoo; an example using the tradename "Biopol" is in the collection of theScience Museum, London.

In 1996, Monsanto (who sold PHB as a copolymer with PHV) bought all patents for making the polymer from ICI/Zeneca including the trademark "Biopol".[5] However, Monsanto's rights to Biopol were sold to the American companyMetabolix in 2001 and Monsanto's fermenters producing PHB from bacteria were closed down at the start of 2004. Monsanto began to focus on producing PHB from plants instead of bacteria.[6] But now with so much media attention on GM crops, there has been little news of Monsanto's plans for PHB.[7]

Biopol is currently used in the medical industry forinternal suture. It is nontoxic and biodegradable, so it does not have to be removed after recovery.[8]

TephaFLEX is a bacterially derived poly-4-hydroxybutyrate, manufactured using a recombinant fermentation process by Tepha Medical Devices, intended for a variety of medical applications that require biodegradable materials such asabsorbable sutures.[9]

Properties

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  • Water-insoluble and relatively resistant to hydrolytic degradation. This differentiates PHB from most other currently availablebiodegradable plastics, which are either water-soluble or moisture-sensitive.
  • Good oxygen permeability.
  • Good ultra-violet resistance but poor resistance to acids and bases.
  • Soluble in chloroform and other chlorinated hydrocarbons.[10]
  • Biocompatible and hence is suitable for medical applications.
  • Melting point 175 °C., and glass transition temperature 2 °C.
  • Tensile strength 40MPa, close to that of polypropylene.
  • Sinks in water (while polypropylene floats), facilitating its anaerobic biodegradation in sediments.
  • Non-toxic.
  • Less 'sticky' when melted.

History

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Polyhydroxybutyrate was first isolated and characterized in 1925 by FrenchmicrobiologistMaurice Lemoigne.[11]

Biodegradation

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Firmicutes and proteobacteria can degrade PHB.Bacillus,Pseudomonas andStreptomyces species can degrade PHB.Pseudomonas lemoigne,Comamonas sp.Acidovorax faecalis,Aspergillus fumigatus andVariovorax paradoxus are soil microbes capable of degradation.Alcaligenes faecalis,Pseudomonas, andIllyobacter delafieldi, are obtained from anaerobic sludge.Comamonas testosteroni andPseudomonas stutzeri were obtained from sea water. Few of these are capable of degrading at higher temperatures; notably excepting thermophilicStreptomyces sp. and a thermophilic strain ofAspergillus sp.[12]

References

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  1. ^Lichtenthaler, Frieder W. (2010). "Carbohydrates as Organic Raw Materials".Ullmann's Encyclopedia of Industrial Chemistry.doi:10.1002/14356007.n05_n07.ISBN 978-3-527-30673-2.
  2. ^Ackermann, Jörg-uwe; Müller, Susann; Lösche, Andreas; Bley, Thomas; Babel, Wolfgang (1995). "Methylobacterium rhodesianum cells tend to double the DNA content under growth limitations and accumulate PHB".Journal of Biotechnology.39 (1):9–20.doi:10.1016/0168-1656(94)00138-3.
  3. ^Steinbüchel, Alexander (2002).Biopolymers, 10 Volumes with Index.Wiley-VCH.ISBN 978-3-527-30290-1.[page needed]
  4. ^Jacquel, Nicolas; Lo, Chi-Wei; Wei, Yu-Hong; Wu, Ho-Shing; Wang, Shaw S. (2008). "Isolation and purification of bacterial poly(3-hydroxyalkanoates)".Biochemical Engineering Journal.39 (1):15–27.Bibcode:2008BioEJ..39...15J.doi:10.1016/j.bej.2007.11.029.
  5. ^"Trade Mark Details"(PDF). 2013-03-28. Retrieved2024-12-30.
  6. ^Poirier, Yves; Somerville, Chris; Schechtman, Lee A.; Satkowski, Michael M.; Noda, Isao (1995). "Synthesis of high-molecular-weight poly([r]-(-)-3-hydroxybutyrate) in transgenic Arabidopsis thaliana plant cells".International Journal of Biological Macromolecules.17 (1):7–12.doi:10.1016/0141-8130(95)93511-U.PMID 7772565.
  7. ^"Plastics You Could Eat". RetrievedNovember 17, 2005.
  8. ^Kariduraganavar, Mahadevappa Y.; Kittur, Arjumand A.; Kamble, Ravindra R. (2014). "Polymer Synthesis and Processing".Natural and Synthetic Biomedical Polymers. pp. 1–31.doi:10.1016/B978-0-12-396983-5.00001-6.ISBN 9780123969835.
  9. ^Tepha Medical Devices Technology Overview
  10. ^Jacquel, Nicolas; Lo, Chi-Wei; Wu, Ho-Shing; Wei, Yu-Hong; Wang, Shaw S. (2007)."Solubility of polyhydroxyalkanoates by experiment and thermodynamic correlations".AIChE Journal.53 (10):2704–14.Bibcode:2007AIChE..53.2704J.doi:10.1002/aic.11274.INIST 19110437.
  11. ^Lemoigne, M (1926). "Produits de dehydration et de polymerisation de l'acide ß-oxobutyrique" [Dehydration and polymerization product of β-oxy butyric acid].Bull. Soc. Chim. Biol. (in French).8:770–82.
  12. ^Tokiwa, Yutaka; Calabia, Buenaventurada P.; Ugwu, Charles U.; Aiba, Seiichi (2009)."Biodegradability of Plastics".International Journal of Molecular Sciences.10 (9):3722–42.doi:10.3390/ijms10093722.PMC 2769161.PMID 19865515.

External links

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