12/18/2019 Polyhydroxyalkanoates - Wikipedia

Polyhydroxyalkanoates
Polyhydroxyalkanoates or
PHAs are polyesters produced in
nature by numerous
microorganisms, including
through bacterial fermentation of
sugars or lipids.[1] When
produced by bacteria they serve Structure of poly-(R)-3-
hydroxybutyrate (P3HB), a
as both a source of energy and as
polyhydroxyalkanoate
a carbon store. More than 150

Chemical structures of P3HB, PHV and their copolymer PHBV

different monomers can be combined within this family to give

materials with extremely different properties.[2] These plastics are
biodegradable and are used in the production of bioplastics.

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They can be either thermoplastic or elastomeric materials, with

melting points ranging from 40 to 180 °C.

The mechanical properties and biocompatibility 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.[3]

Contents
Biosynthesis
Industrial production
Material properties
Applications
References
Further reading

Biosynthesis
To produce PHA, a culture of a micro-organism such as
Cupriavidus necator is 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 is 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.

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The biosynthesis of PHA is

usually caused by certain
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.[4]

Polyesters are deposited in the Certain strains of Bacillus subtilis

bacteria can be used to produce
form of highly refractive
polyhydroxyalkanoates
granules in the cells.
Depending upon the
microorganism and the cultivation conditions, homo- or
copolyesters with different hydroxyalkanic acids are generated.
PHA granules are then recovered by disrupting the cells.[5]
Recombinant Bacillus subtilis str. pBE2C1 and Bacillus subtilis str.
pBE2C1AB were used in production of polyhydroxyalkanoates
(PHA) and it was shown that they could use malt waste as carbon
source for lower cost of PHA production.

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:

Poly (HA SCL) from hydroxy fatty acids with short chain
lengths including three to five carbon atoms are synthesized by
numerous bacteria, including Cupriavidus necator and
Alcaligenes latus (PHB).
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Poly (HA MCL) from hydroxy fatty acids with medium chain
lengths including six to 14 carbon atoms, can be made for
example, by Pseudomonas putida.
A few bacteria, including Aeromonas hydrophila 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 poly-beta-hydroxybutyrate (poly-3-
hydroxybutyrate, P3HB), which consists of 1000 to 30000
hydroxy fatty acid monomers.

Industrial production
In the industrial production of PHA, the polyester is extracted and
purified from the bacteria by optimizing the conditions of
microbial fermentation of sugar or glucose.

In the 1980s, Imperial Chemical Industries developed poly(3-

hydroxybutyrate-co-3-hydroxyvalerate) obtained via fermentation
that was named "Biopol". It was sold under the name "Biopol" and
distributed in the U.S. by Monsanto and later Metabolix.[6]

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
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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
start-up Micromidas[7] and Veolia subsidiary Anoxkaldnes.[8]

PHAs are processed mainly via injection molding, extrusion and

extrusion bubbles into films and hollow bodies.

Material properties
PHA polymers are thermoplastic, can be processed on
conventional processing equipment, and are, depending on their
composition, ductile and more or less elastic. They differ in their
properties according to their chemical composition (homo-or
copolyester, contained hydroxy fatty acids).

They are UV stable, in contrast to other bioplastics from polymers

such as polylactic acid, partial ca. temperatures up to 180 °C, and
show a low permeation of water. The crystallinity can lie in the
range of a few to 70%. Processability, impact strength and
flexibility improves with a higher percentage of valerate in the
material. PHAs are soluble in halogenated solvents such
chloroform, dichloromethane or dichloroethane.[9]

PHB is similar in its material properties to polypropylene (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.

Applications
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Structure of poly-3- Structure of poly-4-

hydroxyvalerate hydroxybutyrate
(PHV) (P4HB)

Due to its biodegradability and potential to create bioplastics with

novel properties, much interest exists to develop the use of PHA-
based materials. PHA fits into the green economy as a means to
create plastics from non-fossil fuel sources. Furthermore, active
research is being carried out for the biotransformation "upcycling"
of plastic waste (e.g., polyethylene terephthalate and
polyurethane) into PHA using Pseudomonas putida bacteria.[10]

A PHA copolymer called PHBV (poly(3-hydroxybutyrate-co-3-

hydroxyvalerate)) is less stiff and tougher, and it may be used as
packaging material.

In June 2005, a US company (Metabolix, Inc.) received the US

Presidential Green Chemistry Challenge Award (small business
category) for their development and commercialisation of a cost-
effective method for manufacturing PHAs.

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There are potential applications for PHA produced by micro-

organisms[2] within the medical and pharmaceutical industries,
primarily due to their biodegradability.

Fixation and orthopaedic applications have included sutures,

suture fasteners, meniscus repair devices, rivets, 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), adhesion barriers, stents, guided tissue
repair/regeneration devices, articular cartilage repair devices,
nerve guides, tendon repair devices, atrial septal defect repair
devices, pericardial patches, bulking and filling agents, vein valves,
bone marrow scaffolds, meniscus regeneration devices, ligament
and tendon grafts, ocular cell implants, spinal fusion cages, skin
substitutes, dural substitutes, bone graft substitutes, bone dowels,
wound dressings, and hemostats.[11]

References
1. Lu, Jingnan; Tappel, Ryan C.; Nomura, Christopher T. (2009-
08-05). "Mini-Review: Biosynthesis of
Poly(hydroxyalkanoates)". Polymer Reviews. 49 (3): 226–248.
doi:10.1080/15583720903048243 (https://doi.org/10.1080%2F
15583720903048243). ISSN 1558-3724 (https://www.worldcat.
org/issn/1558-3724).
2. Doi, Yoshiharu; Steinbuchel, Alexander (2002). Biopolymers.
Weinheim, Germany: Wiley-VCH. ISBN 978-3-527-30225-3.

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3. Michael, Anne John (September 12, 2004).

"Polyhydroxyalkanoates for tissue engineering" (https://web.arc
hive.org/web/20070128234757/http://tissue.medicalengineer.c
o.uk/Polyhydroxyalkanoates+for+tissue+engineering.php).
Archived from the original (http://tissue.medicalengineer.co.uk/
Polyhydroxyalkanoates+for+tissue+engineering.php) on
January 28, 2007.
4. Kim, Y. B.; Lenz, R. W. (2001). "Polyesters from
microorganisms". Advances in Biochemical
Engineering/Biotechnology. 71: 51–79. doi:10.1007/3-540-
40021-4_2 (https://doi.org/10.1007%2F3-540-40021-4_2).
ISBN 978-3-540-41141-3. ISSN 0724-6145 (https://www.worldc
at.org/issn/0724-6145). PMID 11217417 (https://www.ncbi.nlm.
nih.gov/pubmed/11217417).
5. 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. doi:10.1016/j.bej.2007.11.029 (https://doi.org/10.
1016%2Fj.bej.2007.11.029).
6. Ewa Rudnik (3 January 2008). Compostable Polymer Materials
(https://books.google.com/books?id=ZrQwn8XzKlEC&pg=PA2
1). Elsevier. p. 21. ISBN 978-0-08-045371-2. Retrieved 10 July
2012.
7. Martin Lamonica (May 27, 2010). "Micromidas to test sludge-
to-plastic tech" (https://www.cnet.com/news/micromidas-to-test
-sludge-to-plastic-tech/). CNET. Retrieved October 23, 2015.
8. Seb Egerton-Read (September 9, 2015). "A New Way to Make
Plastic" (http://circulatenews.org/2015/09/a-new-way-to-make-
plastic/). Circulate. Retrieved October 23, 2015.
9. 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. doi:10.1002/aic.11274 (https://doi.org/10.100
2%2Faic.11274).
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10. "Homepage - P4SB" (http://www.p4sb.eu/). www.p4sb.eu.

Retrieved 2017-10-26.
11. Chen, Guo-Qiang; Wu, Qiong (2005). "The application of
polyhydroxyalkanoates as tissue engineering materials".
Biomaterials. 26 (33): 6565–78.
doi:10.1016/j.biomaterials.2005.04.036 (https://doi.org/10.101
6%2Fj.biomaterials.2005.04.036). PMID 15946738 (https://ww
w.ncbi.nlm.nih.gov/pubmed/15946738).

Further reading
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.
doi:10.1080/09593330.2017.1291759 (https://doi.org/10.108
0%2F09593330.2017.1291759). PMID 28162048 (https://www.
ncbi.nlm.nih.gov/pubmed/28162048).
Mohapatra, Swati; Maity, Sudipta; Dash, Hirak Ranjan; Das,
Surajit; Pattnaik, Swati; Rath, Chandi Charan; Samantaray,
Deviprasad (December 2017). "Bacillus and biopolymer:
Prospects and challenges" (https://www.ncbi.nlm.nih.gov/pmc/
articles/PMC5651552). Biochemistry and Biophysics Reports.
12: 206–13. doi:10.1016/j.bbrep.2017.10.001 (https://doi.org/1
0.1016%2Fj.bbrep.2017.10.001). PMC 5651552 (https://www.n
cbi.nlm.nih.gov/pmc/articles/PMC5651552). PMID 29090283 (h
ttps://www.ncbi.nlm.nih.gov/pubmed/29090283).

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