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<title>Polyhydroxyalkanoates</title>

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Polyhydroxyalkanoates

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Polyhydroxyalkanoates or PHAs are <a href="Polyester" title="Polyester">polyesters</a> produced in nature by numerous microorganisms, including through <a href="Bacteria" title="Bacteria">bacterial</a> <a href="Fermentation_(biochemistry)" class="mw-redirect" title="Fermentation (biochemistry)">fermentation</a> of <a href="Sugar" title="Sugar">sugars</a> or <a href="Lipid" title="Lipid">lipids</a>.<a href="#cite_note-1">[1]</a> When produced by bacteria they serve as both a source of energy and as a carbon store. More than 150 different <a href="Monomer" title="Monomer">monomers</a> can be combined within this family to give materials with extremely different properties.<a href="#cite_note-doi-2002-2">[2]</a> These plastics are biodegradable and are used in the production of <a href="Bioplastics" class="mw-redirect" title="Bioplastics">bioplastics</a>.<a href="#cite_note-3">[3]</a>

They can be either <a href="Thermoplastic" title="Thermoplastic">thermoplastic</a> or <a href="Elastomer" title="Elastomer">elastomeric</a> materials,<a href="#cite_note-q776-4">[4]</a> with <a href="Melting_point" title="Melting point">melting points</a> ranging from 40 to 180 °C.

The mechanical properties and <a href="Biocompatibility" title="Biocompatibility">biocompatibility</a> of PHA can also be changed by blending, modifying the surface or combining PHA with other polymers, enzymes and inorganic materials, making it possible for a wider range of applications.<a href="#cite_note-5">[5]</a>

<div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2></div>

To induce PHA production in a laboratory setting, a culture of a micro-organism such as <a href="Cupriavidus_necator" title="Cupriavidus necator">Cupriavidus necator</a> can be placed in a suitable medium and fed appropriate nutrients so that it multiplies rapidly. Once the population has reached a substantial level, the nutrient composition can be changed to force the micro-organism to synthesize PHA. The yield of PHA obtained from the intracellular granule inclusions can be as high as 80% of the organism's dry weight.

The biosynthesis of PHA is usually caused by deficiency conditions (e.g. lack of macro elements such as phosphorus, nitrogen, trace elements, or lack of oxygen) and the excess supply of carbon sources.<a href="#cite_note-6">[6]</a> However, the prevalence of PHA production within either a mono-culture or a set of mixed-microbial organisms can also be dependent on overall nutrient limitation, not just macro elements. This is especially the case in the 'feast/famine' cycle method for induction of PHA production, wherein carbon is periodically added and depleted to cause famine, which encourages cells to produce PHA during 'feast' as a storage method for periods of famine.

Polyesters are deposited in the form of highly refractive granules in the cells. Depending upon the microorganism and the cultivation conditions, homo- or <a href="Copolyester" title="Copolyester">copolyesters</a> with different hydroxyalkanoic acids are generated. PHA granules are then recovered by disrupting the cells.<a href="#cite_note-7">[7]</a> Recombinant <a href="Bacillus_subtilis" title="Bacillus subtilis">Bacillus subtilis</a> str. pBE2C1 and Bacillus subtilis str. pBE2C1AB were used in production of polyhydroxyalkanoates (PHA) and it was shown that they could use <a href="Malt" title="Malt">malt</a> waste as carbon source for lower cost of PHA production.<a href="#cite_note-8">[8]</a>

PHA synthases are the key enzymes of PHA biosynthesis. They use the coenzyme A - thioester of (r)-hydroxy fatty acids as substrates. The two classes of PHA synthases differ in the specific use of hydroxy fatty acids of short or medium chain length.

The resulting PHA is of the two types:

<ul><li>Poly (HA SCL) from hydroxy fatty acids with short chain lengths including three to five carbon atoms are synthesized by numerous bacteria, including <a href="Cupriavidus_necator" title="Cupriavidus necator">Cupriavidus necator</a> and <a href="Alcaligenes_latus" class="mw-redirect" title="Alcaligenes latus">Alcaligenes latus</a> (<a href="Polyhydroxybutyrate" title="Polyhydroxybutyrate">PHB</a>).</li>

<li>Poly (HA MCL) from hydroxy fatty acids with medium chain lengths including six to 14 carbon atoms, can be made for example, by <a href="Pseudomonas_putida" title="Pseudomonas putida">Pseudomonas putida</a>.</li></ul>

A few bacteria, including <a href="Aeromonas_hydrophila" title="Aeromonas hydrophila">Aeromonas hydrophila</a> and Thiococcus pfennigii, synthesize copolyester from the above two types of hydroxy fatty acids, or at least possess enzymes that are capable of part of this synthesis.

Another even larger scale synthesis can be done with the help of soil organisms. For lack of nitrogen and phosphorus they produce a kilogram of PHA per three kilograms of sugar.

The simplest and most commonly occurring form of PHA is the fermentative production of <a href="Polyhydroxybutyrate" title="Polyhydroxybutyrate">poly-beta-hydroxybutyrate</a> [poly(3-hydroxybutyrate), P(3HB)], which consists of 1000 to 30000 hydroxy fatty acid monomers.

<div class="mw-heading mw-heading2"><h2 id="Industrial_production">Industrial production</h2></div>

In the industrial production of PHA, the polyester is extracted and purified from the bacteria by optimizing the conditions of microbial fermentation of <a href="Sugar" title="Sugar">sugar</a>, <a href="Glucose" title="Glucose">glucose</a>, or <a href="Vegetable_oil" title="Vegetable oil">vegetable oil</a>.

In the 1980s, <a href="Imperial_Chemical_Industries" title="Imperial Chemical Industries">Imperial Chemical Industries</a> developed <a href="Poly(3-hydroxybutyrate-co-3-hydroxyvalerate)" class="mw-redirect" title="Poly(3-hydroxybutyrate-co-3-hydroxyvalerate)">poly(3-hydroxybutyrate-co-3-hydroxyvalerate)</a> obtained via fermentation that was named "Biopol". It was sold under the name "Biopol" and distributed in the U.S. by <a href="Monsanto" title="Monsanto">Monsanto</a> and later <a href="Metabolix" class="mw-redirect" title="Metabolix">Metabolix</a>.<a href="#cite_note-Rudnik2008-9">[9]</a>

As raw material for the fermentation, carbohydrates such as glucose and sucrose can be used, but also vegetable oil or glycerine from biodiesel production. Researchers in industry are working on methods with which transgenic crops will be developed that express PHA synthesis routes from bacteria and so produce PHA as energy storage in their tissues. Several companies are working to develop methods of producing PHA from waste water, including <a href="Veolia" title="Veolia">Veolia</a> subsidiary Anoxkaldnes.<a href="#cite_note-10">[10]</a> and start-ups, Micromidas,<a href="#cite_note-11">[11]</a> Mango Materials,<a href="#cite_note-12">[12]</a><a href="#cite_note-13">[13]</a> Full Cycle Bioplastics,<a href="#cite_note-14">[14]</a> Newlight and <a rel="nofollow" class="external text" href="https://www.paquesbiomaterials.nl/">Paques Biomaterials</a>.<a href="#cite_note-15">[15]</a><a href="#cite_note-16">[16]</a>

PHAs are processed mainly via injection molding, extrusion and extrusion bubbles into films and hollow bodies.

<div class="mw-heading mw-heading2"><h2 id="Material_properties">Material properties</h2></div>

PHA polymers are thermoplastic, can be processed on conventional processing equipment, and are, depending on their composition, ductile and more or less elastic.<a href="#cite_note-17">[17]</a> They differ in their properties according to their chemical composition (homo-or copolyester, contained hydroxy fatty acids).

They are <a href="Ultraviolet" title="Ultraviolet">UV</a> stable, in contrast to other bioplastics from polymers such as <a href="Polylactic_acid" title="Polylactic acid">polylactic acid</a>, partial ca. temperatures up to 180 °C, and show a low permeation of water. The <a href="Crystallinity" title="Crystallinity">crystallinity</a> can lie in the range of a few to 70%. Processability, impact strength and flexibility improves with a higher percentage of <a href="Valeric_acid#Valerate_salts_and_esters" title="Valeric acid">valerate</a> in the material. PHAs are soluble in halogenated solvents such <a href="Chloroform" title="Chloroform">chloroform</a>, <a href="Dichloromethane" title="Dichloromethane">dichloromethane</a> or <a href="Dichloroethane" title="Dichloroethane">dichloroethane</a>.<a href="#cite_note-18">[18]</a>

PHB is similar in its material properties to <a href="Polypropylene" title="Polypropylene">polypropylene</a> (PP), has a good resistance to moisture and aroma barrier properties. Polyhydroxybutyric acid synthesized from pure PHB is relatively brittle and stiff. PHB copolymers, which may include other fatty acids such as beta-hydroxyvaleric acid, may be elastic.

<div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2></div>

<div class="gallerytext">Structure of poly-3-hydroxyvalerate (PHV)</div>

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<div class="gallerytext">Structure of poly-4-hydroxybutyrate (P4HB)</div>

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Due to its <a href="Biodegradability" class="mw-redirect" title="Biodegradability">biodegradability</a> and potential to create <a href="Bioplastic" title="Bioplastic">bioplastics</a> with novel properties, much interest exists to develop the use of PHA-based materials. PHA fits into the <a href="Green_economy" title="Green economy">green economy</a> as a means to create plastics from non-fossil fuel sources. Furthermore, active research is being carried out for the <a href="Biotransformation" title="Biotransformation">biotransformation</a> "<a href="Upcycling" title="Upcycling">upcycling</a>" of <a href="Plastic_waste" class="mw-redirect" title="Plastic waste">plastic waste</a> (e.g., <a href="Polyethylene_terephthalate" title="Polyethylene terephthalate">polyethylene terephthalate</a> and <a href="Polyurethane" title="Polyurethane">polyurethane</a>) into PHA using <a href="Pseudomonas_putida" title="Pseudomonas putida">Pseudomonas putida</a> bacteria.<a href="#cite_note-19">[19]</a>

A PHA copolymer called <a href="PHBV" title="PHBV">PHBV</a> (poly(3-hydroxybutyrate-co-3-hydroxyvalerate)) is less stiff and tougher, and it may be used as packaging material.

In June 2005, US company <a href="Metabolix" class="mw-redirect" title="Metabolix">Metabolix</a>, Inc. received the US <a href="Presidential_Green_Chemistry_Challenge_Award" class="mw-redirect" title="Presidential Green Chemistry Challenge Award">Presidential Green Chemistry Challenge Award</a> (small business category) for their development and commercialisation of a cost-effective method for manufacturing PHAs.<a href="#cite_note-20">[20]</a>

There are potential applications for PHA produced by micro-organisms<a href="#cite_note-doi-2002-2">[2]</a> within the agricultural,<a href="#cite_note-21">[21]</a> medical and pharmaceutical industries, primarily due to their biodegradability.

Fixation and orthopaedic applications have included <a href="Surgical_suture" title="Surgical suture">sutures</a>, suture fasteners, <a href="Meniscus_(anatomy)" title="Meniscus (anatomy)">meniscus</a> repair devices, <a href="Rivet" title="Rivet">rivets</a>, tacks, staples, screws (including interference screws), bone plates and bone plating systems, surgical mesh, repair patches, slings, cardiovascular patches, orthopedic pins (including bone.lling augmentation material), <a href="Adhesion_barrier" title="Adhesion barrier">adhesion barriers</a>, <a href="Stent" title="Stent">stents</a>, guided tissue repair/regeneration devices, articular <a href="Cartilage" title="Cartilage">cartilage</a> repair devices, nerve guides, <a href="Tendon" title="Tendon">tendon</a> repair devices, <a href="Atrial_septal_defect" title="Atrial septal defect">atrial septal defect</a> repair devices, pericardial patches, bulking and filling agents, <a href="Vein" title="Vein">vein</a> valves, <a href="Bone_marrow" title="Bone marrow">bone marrow</a> scaffolds, meniscus regeneration devices, <a href="Ligament" title="Ligament">ligament</a> and tendon grafts, <a href="Human_eye" title="Human eye">ocular</a> cell implants, spinal fusion cages, skin substitutes, <a href="Dura_mater" title="Dura mater">dural</a> substitutes, bone graft substitutes, bone dowels, wound dressings, and <a href="Hemostat" title="Hemostat">hemostats</a>.<a href="#cite_note-22">[22]</a>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

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</ol></div></div>

<div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2></div>

<ul><li><cite id="CITEREFMohapatraSarkarSamantarayDaware2017" class="citation journal cs1">Mohapatra, S.; Sarkar, B.; Samantaray, D. P.; Daware, A.; Maity, S.; Pattnaik, S.; Bhattacharjee, S. (2017). "Bioconversion of fish solid waste into PHB using Bacillus subtilis based submerged fermentation process". Environmental Technology. 38 (24): 1–8. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2017EnvTe..38.3201M">2017EnvTe..38.3201M</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F09593330.2017.1291759">10.1080/09593330.2017.1291759</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/28162048">28162048</a>. <a href="S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:1080507">1080507</a>.</cite></li>

<li><cite id="CITEREFMohapatraMaityDashDas2017" class="citation journal cs1">Mohapatra, Swati; Maity, Sudipta; Dash, Hirak Ranjan; Das, Surajit; Pattnaik, Swati; Rath, Chandi Charan; Samantaray, Deviprasad (December 2017). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5651552">"Bacillus and biopolymer: Prospects and challenges"</a>. Biochemistry and Biophysics Reports. 12: 206–13. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.bbrep.2017.10.001">10.1016/j.bbrep.2017.10.001</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5651552">5651552</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29090283">29090283</a>.</cite></li></ul>

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