Methods for Analysis of Poly(3-hydroxyalkanoate) (PHA) Composition
Ing. Theo C. de Rijk
- [email protected]
- +31-317-475400 | Fax: +31-317-417717
State Institute for Quality Control of Agricultural Products (RIKILT), PO Box 230, Bornsesteeg 45, Wageningen, The Netherlands, NL-6700 AE
Search for more papers by this authorIng. Pieter van de Meer
- [email protected]
- +31-317-475300 | Fax: +31-317-475347
Agrotechnological Research Institute (ATO), PO Box 17, 6700 AA, Bornsesteeg 59, Wageningen, The Netherlands, NL-6700 AE
Search for more papers by this authorDr. Gerrit Eggink
- [email protected]
- +31-317-475300 | Fax: +31-317-475347
Agrotechnological Research Institute (ATO), PO Box 17, 6700 AA, Bornsesteeg 59, Wageningen, The Netherlands, NL-6700 AE
Search for more papers by this authorDr. Ruud A. Weusthuis
- [email protected]
- +31-317-475300 | Fax: +31-317-475347
Agrotechnological Research Institute (ATO), PO Box 17, 6700 AA, Bornsesteeg 59, Wageningen, The Netherlands, NL-6700 AE
Search for more papers by this authorIng. Theo C. de Rijk
- [email protected]
- +31-317-475400 | Fax: +31-317-417717
State Institute for Quality Control of Agricultural Products (RIKILT), PO Box 230, Bornsesteeg 45, Wageningen, The Netherlands, NL-6700 AE
Search for more papers by this authorIng. Pieter van de Meer
- [email protected]
- +31-317-475300 | Fax: +31-317-475347
Agrotechnological Research Institute (ATO), PO Box 17, 6700 AA, Bornsesteeg 59, Wageningen, The Netherlands, NL-6700 AE
Search for more papers by this authorDr. Gerrit Eggink
- [email protected]
- +31-317-475300 | Fax: +31-317-475347
Agrotechnological Research Institute (ATO), PO Box 17, 6700 AA, Bornsesteeg 59, Wageningen, The Netherlands, NL-6700 AE
Search for more papers by this authorDr. Ruud A. Weusthuis
- [email protected]
- +31-317-475300 | Fax: +31-317-475347
Agrotechnological Research Institute (ATO), PO Box 17, 6700 AA, Bornsesteeg 59, Wageningen, The Netherlands, NL-6700 AE
Search for more papers by this authorAbstract
- Introduction
- Historical Outline
- Analytical Methods
- Analysis of SCL-PHAs
- GC and MS
- NMR
- HPLC
- Analysis of other PHA
- GC
- MS
- NMR
- Outlook and Perspectives
- Acknowledgements
References
- Abe, C., Taima, Y., Nakamura, Y., Doi, Y. (1990) New bacterial copolyester of 3-hydroxyalkanoates and 3-hydroxy-ω-fluoroalkanoates produced by Pseudomonas oleovorans, Polym. Commun. 31, 404–406.
- Abe, H., Doi, Y., Fukushima, T., Eya, H. (1994) Biosynthesis from gluconate of random copolyester consisting of 3-hydroxybutyrate and medium-chain-length 3-hydroxyalkanoates by Pseudomonas sp. 61-3, Int. J. Biol. Macromol. 16, 115–119.
- Anderson, A. J., Williams, D. R., Dawes, A. E., Ewing, D. F. (1995) Biosynthesis of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) in Rhodococcus ruber, Can. J. Microbiol. 41, 4–13.
- Bear, M. M., Leboucher-Durand, M. A., Langlois, V., Lenz, R. W., Goodwin, S., Guérin, P. (1997) Bacterial poly-3-hydroxyalkenoates with epoxy groups in the side chain, Reactive Funct. Polym. 34, 65–77.
- Bear, M. M., Mallarde, D., Langlois, V., Langlois, V., Randriamahefa, S., Guérin, P. (1999) Natural and artificial functionalized biopolyesters. II. Medium-chain length polyhydroxyoctanoates from Pseudomonas strains, J. Environ. Polym. Degrad. 7, 179–184.
- Bligh, E. G., Dyer, W. J. (1959) A rapid method of total lipid extraction and purification, Can. J. Biochem. Physiol. 37, 911–917.
- Brandl, H., Gross, R. A., Lenz, R. W., Fuller, R. C. (1988) Pseudomonas oleovorans as a source of poly(β-hydroxyalkanoates) for potential applications as biodegradeable polymers, Appl. Environ. Microbiol. 54, 1977–1982.
- Braunegg, G., Sonnleitner, B., Lafferty, R. M. (1978) A rapid method for the determination of poly-β-hydroxybutyric acid in microbial biomass, Eur. J. Appl. Microbiol. 6, 29–37.
- Capon, R. J., Dunlop, R. W., Ghisalberti, E. L., Jefferies, P. R. (1983) Poly-3-hydroxyalkanoates from marine and freshwater cyanobacteria, Phytochemistry 22, 1181–1184.
- Casini, E., De Rijk, T. C., De Waard, P., Eggink, G. (1997) Synthesis of poly(hydroxyalkanoate) from hydrolyzed linseed oil, J. Environ. Polym. Degrad. 5, 153–158.
- Chapman, J. R. (1993) Practical Organic Mass Spectrometry, 2nd edition, New York: John Wiley & Sons.
- Choi, M. H., Yoon, S. C. (1994) Polyester biosynthesis characteristics of Pseudomonas citronellolis grown on various carbon sources, including 3-methyl-branched substrates, Appl. Environ. Microbiol. 60, 3245–3254.
- Comeau, Y., Hall, K. J., Oldham, W. K. (1988) Determination of poly-β-hydroxybutyrate and poly-β-hydroxyvalerate in activated sludge by gas-liquid chromatography, Appl. Environ. Microbiol. 54, 2325–2327.
- Cromwick, A.-M., Foglia, T., Lenz, R. W. (1996) The microbial production of poly(hydroxyalkanoates) from tallow, Appl. Microbiol. Biotechnol. 46, 464–469.
- Curley, J. M., Lenz, R. W., Fuller, R. C., Browne, S. E., Panday, S. (1997) C13 NMR spectroscopy in living cells of Pseudomonas oleovorans, Polymer 38, 5313–5319.
-
Del Don, C.,
Hanselmann, K. W.,
Peduzzi, R.,
Bachofen, R.
(1994)
Biomass composition and methods for the determination of metabolic reserve polymers in phototrophic sulfur bacteria,
Aquatic Sci. 56,
1–15.
10.1007/BF00877431 Google Scholar
- De Smet, M. J., Eggink, G., Witholt, B., Kingma, J., Wynberg, H. (1983) Characterization of intracellular inclusions formed by Pseudomonas oleovorans during growth on octane, J. Bacteriol. 154, 870–878.
- De Waard, P., Van der Wal, H., Huijberts, G. N. M., Eggink, G. (1993) Heteronuclear NMR analysis of unsaturated fatty acids in poly(3-hydroxyalkanoates), J. Biol. Chem. 268, 315–319.
- Doi, Y., Abe, C. (1990) Biosynthesis and characterization of a new bacterial copolyester of 3-hydroxyalkanoates and 3-hydroxy-ω-chloroalkanoates, Macromol. 23, 3705–3707.
- Doi, Y., Kunioka, M., Nakamura, Y., Soga, K. (1986) Nuclear magnetic resonance studies on poly(β-hydroxybutyrate) and a copolyester of β-hydroxybutyrate and β-hydroxyvalerate isolated from Alcaligenes eutrophus H16, Macromolecules 19, 2860–2864.
- Doi, Y., Tamaki, A., Kunioka, M., Soga, K. (1987) Biosynthesis of terpolyesters of 3-hydroxybutyrate, 3-hydroxyvalerate and 5-hydroxyvalerate from 5-chloropentanoic and pentanoic acids, Macromol. Chem. Rapid Commun. 8, 631–635.
- Doi, Y., Kunioka, M., Nakamura, Y., Soga, K. (1988) Nuclear magnetic resonance studies on unusual bacterial copolyesters of 3-hydroxybutyrate and 4-hydroxybutyrate, Macromolecules 21, 2722–2727.
- Doi, Y., Segawa, A., Kunioka, M. (1990a) Biosynthesis and characterization of poly(3-hydroxybutyrate-co-4-hydroxybutyrate) in Alcaligenes eutrophus, Int. J. Biol. Macromol. 12, 106–111.
- Doi, Y., Segawa, A., Nakamura, S., Kunioka, M. (1990b) Production of biodegradeable copolyesters by Alcaligenes eutrophus, in: Novel Biosynthetic Biodegradable Polymers of Industrial Interest from Microorganisms ( A. E. Dawes, Ed.), Dordrecht: Kluwer, 37–48.
- Doi, Y., Kitamura, S., Abe, H. (1995) Microbial synthesis and characterization of poly(3-hydroxybutyrate-co-hydroxyhexanoate), Macromolecules 28, 4822–4828.
- Eggink, G., de Waard, P., Huijberts, G. N. M. (1992) The role of fatty acid biosynthesis and degradation in the supply of substrates for poly(3-hydroxyalkanoate) formation in Pseudomonas putida, FEMS Microbiol. Rev. 103, 159–164
- Eggink, G., De Waard, P., Huijberts, G. N. M. (1995) Formation of novel poly(3-hydroxyalkanoates) from long chain fatty acids, Can. J. Microbiol. 41, 14–21.
- Findlay, R. H., White, D. C. (1983) Polymeric beta-hydroxyalkanoates from environmental samples and Bacillus megaterium, Appl. Environ. Microbiol. 45, 71–78.
- Friebolin, H. (1991) Basic One- and Two-Dimensional NMR Spectroscopy, Weinheim, Germany: VCH.
- Fritzsche, K., Lenz, R. W. (1990) An unusual bacterial polyester with a phenyl pendant group, Makromol. Chem. 191, 1957–1965.
- Fritzsche, K., Lenz, R. W., Fuller, R. C. (1990a) Production of unsaturated polyesters by Pseudomonas oleovorans, Int. J. Biol. Macromol. 12, 85–91.
- Fritzsche, K., Lenz, R. W., Fuller, R. C. (1990b) Bacterial polyesters containing branched poly(β-hydroxyalkanoate) units, Int. J. Biol. Macromol. 12, 92–101.
- Füchtenbusch, B. D., Steinbüchel, A. (1999) Biosynthesis of polyhydroxyalkanoates from low-rank coal liquefaction products by Pseudomonas oleovorans and Rhodococcus ruber, Appl. Microbiol. Biotechnol. 52, 91–95.
- Füchtenbusch, B., Fabritius, D., Steinbüchel, A. (1996) Incorporation of 2-methyl-3-hydroxybutyric acid into polyhydroxyalkanoic acids by axenic cultures in defined media, FEMS Microbiol. Lett. 138, 153–160.
- Füchtenbusch, B., Fabritius, D., Wältermann, M., Steinbüchel, A. (1998) Biosynthesis of novel copolyesters containing 3-hydroxypivalic acid by Rhodococcus ruber NCIMB 40126 and related bacteria, FEMS Microbiol. Lett. 159, 85–92.
- Füchtenbusch, B., Wullbrandt, D., Steinbüchel, A. (2000) Production of polyhydroxyalkanoic acids by Ralstonia eutropha and Pseudomonas oleovorans from an oil remaining from biotechnological rhamnose production, Appl. Microbiol. Biotechnol. 53, 167–172.
- Fukui, T., Kato, M., Matsusaki, H., Iwata, T., Doi, Y. (1998) Morphological and 13C-nuclear magnetic resonance studies for polyhydroxyalkanoate biosynthesis in Pseudomonas sp. 61-3, FEMS Microbiol. Lett. 164, 219–225.
- Gerngross, T. U., Martin, D. P. (1995) Enzyme-catalyzed synthesis of poly[(R)-(–)-3-hydroxybutyrate]: formation of macroscopic granules in vitro, Proc. Natl Acad. Sci. USA 92, 6279–6283.
- Grob, R. L. (Ed.) (1995) Modern Practice of Gas Chromatography, 3rd edition, New York: John Wiley & Sons.
- Gross, R. A., DeMello, C., Lenz, R. W., Brandl, H., Fuller, R. C. (1989) Biosynthesis and characterization of poly(β-hydroxyalkanoates) produced by Pseudomonas oleovorans, Macromolecules 22, 1106–1115.
- Gross, R. A., Kim, O., Rutherford, D. R., Newmark, R. A. (1996) Cyanophenoxy- containing microbial polyesters: Structural analysis, thermal properties, second harmonic generation and in-vivo biodegradability, Polym. Int. 39, 205–213.
- Günther, H. (1995) NMR Spectroscopy, 2nd edition, New York: John Wiley & Sons.
- Hahn, J. J., Eschenlauer, A. C., Sleytr, U. B., Somers, D. A., Srienc, F. (1999) Peroxisomes as sites for synthesis of polyhydroxyalkanoates in transgenic plants, Biotechnol. Progr. 15, 1053–1057.
- Haywood, G. W., Anderson, A. J., Dawes, E. A. (1989) A survey of the accumulation of novel polyhydroxyalkanoates by bacteria, Biotechnol. Lett. 11, 471–476.
- Hazer, B., Lenz, R. W., Fuller, R. C. (1994) Biosynthesis of methyl-branched poly(β-hydroxyalkanoate)s by Pseudomonas oleovorans, Macromolecules 27, 45–49.
- Hazer, B., Lenz, R. W., Fuller, R. C. (1996) Bacterial production of poly-3-hydroxyalkanoates containing arylalkyl substituent groups, Polymer 37, 5951–5957.
- He, W., Tian, W., Zhang, G., Chan, G. Q., Zhang, Z. (1998) Production of novel polyhydroxyalkanoates by Pseudomonas stutzeri 1317 from glucose and soybean oil, FEMS Microbiol. Lett. 169, 45–49.
- Hesselmann, R. P. X., Fleischmann, T., Hany, R., Zehnder, A. J. B. (1999) Determination of polyhydroxyalkanoates in activated sludge by ion chromatographic and enzymatic methods, J. Microbiol. Methods 35, 111–119.
- Huijberts, G. N. M., Eggink, G., De Waard, P., Huisman, G. W., Withold, B. (1992) Pseudomonas putida KT2442 cultivated on glucose accumulates poly(3-hydroxyalkanoates) (PHAs) consisting of saturated and unsaturated monomers, Appl. Environ. Microbiol. 58, 536–544.
- Huijberts, G. N. M., De Rijk, T. C., De Waard, P., Eggink, G. (1994a) 13C Nuclear Magnetic Resonance studies of Pseudomonas putida fatty acid metabolic routes involved in poly(3-hydroxyalkanoate) synthesis, J. Bacteriol. 176, 1661–1666.
- Huijberts, G. N. M., Van der Wal, H., Wilkinson, C., Eggink, G. (1994b) Gas-chromatographic analysis of poly(3-hydroxyalkanoates) in bacteria, Biotechnol. Tech. 8, 187–192.
- Jan, S., Roblot, C., Goethals, G., Courtois, J., Courtois, B., Saucedo, B., Seguin, J., Barbotin, J. (1995) Study of parameters affecting poly(3-hydroxybutyrate) quantification by gas chromatography, Anal. Biochem. 225: 258–263.
- Jan, S., Roblot, C., Courtois, J., Barbotin, J. N., Séguin, J. P. (1996) 1H NMR spectroscopic determination of poly 3-hydroxybutyrate extracted from microbial biomass, Enzyme Microbial Technol. 18, 195–201.
- Jossek, R., Reichelt, R., Steinbüchel, A. (1998) In vitro biosynthesis of poly(3-hydroxybutyric acid) by using purified poly(hydroxyalkanoic acid) synthase from Chromatium vinosum, Appl. Microbiol. Biotechnol. 49, 258–266.
- Jung, K., Hany, R., Rentsch, D., Storni, T., Egli, T., Witholt, B. (2000) Characterization of new bacterial copolyesters containing 3-hydroxyoxoalkanoates and acetoxy-3-hydroxyalkanoates, Macromolecules 33, 8571–8575.
- Jüttner, R. R., Lafferty, R. M., Knackmuss, H. J. (1975) A simple method for the determination of poly-β-hydroxybutyric acid in microbial biomass, Eur. J. Appl. Microbiol. Biotechnol. 1, 233–237.
- Karr, D. B., Waters, J. K., Emerich, D. W. (1983) Analysis of poly-β-hydroxybutyrate in Rhizobium japonicum bacteroids by ion-exclusive high pressure liquid chromatography and UV-dectection, Appl. Environ. Microbiol. 46, 1339–1344.
- Kato, M., Bao, H. J., Kang, C. K., Fukui, T., 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.
- Kellerhals, M. B., Kessler, B., Withold, B. (2000) Renewable long-chain fatty acids for production of biodegradable medium-chain-length polyhydroxyalkanoates (mcl-PHAs) at laboratory and pilot plant scales, Macromolecules 33, 4690–4698.
- Kim, D. Y., Kim, Y. B., Rhee, Y. H. (2000) Evaluation of various carbon substrates for the biosynthesis of polyhydroxyalkanoates bearing functional groups by Pseudomonas putida, Int. J. Biol. Macromol. 28, 23–29.
- Kim, O., Gross, R. A., Rutherford, D. R. (1994) Bioengineering of poly (β-hydroxyalkanoates) for advanced material applications: incorporation of cyano and nitrophenoxy side chain constituents, Can. J. Microbiol. 41, 32–43.
- Kim, O., Gross, R. A., Hammer, W. J., Newmark, R. A. (1996) Microbial synthesis of poly(β-hydroxyalkanoates) containing fluorinated side-chain substituents, Macromolecules 29, 4572–4581.
- Kim, Y. B., Lenz, R. W., Fuller, R. C. (1991) Preparation and characterization of poly(β-hydroxyalkanoates) obtained from Pseudomonas oleovorans grown with mixtures of 5-phenylvaleric acid and n-alkanoic acids, Macromolecules 24, 5256–5260.
- Kim, Y. B., Fuller, R. C. (1992) Poly(β-hydroxyalkanoate) copolymers containing brominated repeating units produced by Pseudomonas oleovorans, Macromol. 25, 1852–1857.
- Kim, Y. B., Rhee, Y. H., Lenz, R. W. (1997) Poly(3-hydroxyalkanoate)s produced by Pseudomonas oleovorans grown by feeding nonanoic acid and 10-undecenoic acid in sequence, Polymer-Journal 29, 894–898.
- Kim, Y. B., Kim, D. Y., Rhee, Y. H. (1999) PHAs produced by Pseudomonas putida and Pseudomonas oleovorans grown with n-alkanoic acids containing aromatic groups, Macromolecules 32, 6058–6064.
- Klinke, S., Ren, Q., Witholt, B., Kessler, B. (1999) Production of medium-chain-length poly(3-hydroxyalkanoates) from gluconate by recombinant Escherichia coli, Appl. Environ. Microbiol. 65, 540–548.
- Kunioka, M., Nakamura, Y., Doi, Y. (1988) New bacterial copolyesters produced in Alcaligenes eutrophus from organic acids, Polym. Commun. 29, 174–176.
- Lageveen, R. G., Huisman, G. W., Preusting, H., Ketelaar, P., Eggink, G., Witholt, B. (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.
- Law, J. H., Slepecky, R. A. (1961) Assay of poly-β-hydroxybutyric acid, J. Bacteriol. 82, 33–36.
- Lee, E. Y., Choi, C. Y. (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.
- Lee, E. Y., Jendrossek, D., Schirmer, A., Choi, C. Y., Steinbüchel, A. (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, App. Microbiol. Biotechnol. 42, 901–909.
- Lee, E. Y., Choi, W. J., Steinbüchel, A., Choi, C. Y. (1996) Cell-recycle fed-batch production of a highly unsaturated polyhydroxyalkanoate from 1,3-butanediol by Pseudomonas sp. A33, J. Environ. Polymer Degrad. 4, 103–112.
- Lemoigne, M. (1926) Produits de déshydration et de polymérization de l'acid β-oxybutyrique, Bull. Soc. Chim. Biol. 8, 770–782.
- Lenz, R. W., Kim, B. W., Ulmer, H. W., Fritzsche, K. (1990) Functionalized poly-β-hydroxyalkanoates produced by bacteria, in: Novel Biosynthetic Biodegradable Polymers of Industrial Interest from Microorganisms ( A. E. Dawes, Ed.), Dordrecht: Kluwer, 23–35.
- Lenz, R. W., Kim, Y. B., Fuller, R. C. (1992) Production of unusual bacterial polyesters by Pseudomonas oleovorans through cometabolism, FEMS Microbiol. Rev. 103, 207–214.
- Lindsay, S. (1992) High Performance Liquid Chromatography, New York: John Wiley & Sons.
- Liu, S. J., Steinbüchel, A. (2000) A novel genetically engineered pathway for synthesis of poly(hydroxyalkanoic acids) in Escherichia coli, Appl. Environ. Microbiol. 66, 739–743.
- Louie, T. M., Mah, T. J., Oldham, W., Ramey, W. D. (2000) Use of metabolic inhibitors and gas chromatography/mass spectrometry to study poly-β-hydroxyalkanoates metabolism involving cryptic nutrients in enhanced biological phosphorus removal systems, Water Res. 34, 1507–1514.
- Madden, L. A., Anderson, A. J., Shah, D. T., Asrar, J. (1999) Chain termination in polyhydroxyalkanoate synthesis: involvement of exogenous hydroxy-compounds as chain transfer agents, Int. J. Biol. Macromol. 25, 43–55.
- Madden, L. A., Anderson, A. J., Asrar, J., Berger, P., Garret, P. (2000) Production and characterization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate-co-4-hydroxybutyrate) synthesized by Ralstonia eutropha in fed-batch cultures, Polymer 41, 3499–3505.
- Matsusaki, H., Abe, H., Taguchi, K., Fukui, T., Doi, Y. (2000) Biosynthesis of poly(3-hydroxybutyrate-co-3-hydroxyalkanoates) by recombinant bacteria expressing the PHA synthase gene phaC1 from Pseudomonas sp. 61-3, Appl. Microbiol. Biotechnol. 53, 401–409.
- McLafferty, F. W., Turecek, F. (1993) Interpretation of Mass Spectra, 4th edition, Mill Valley, CA: University Science Books.
- Morikawa, H., Marchessault, R. H. (1981) Pyrolysis of bacterial polyhydroxyalkanoates, Can. J. Chem. 59, 2306–2313.
- Odham, G., Tunlid, A., Westerdahl, G., Mården, P. (1986) Combined determination of poly-β-hydroxyalkanoic and cellular fatty acids in starved marine bacteria and sewage sludge by gas chromatography with flame ionization or mass spectrometry detection, Appl. Environ. Microbiol. 52, 905–910.
- Parry, E. A. J., Robinson, D. S., Wedzicka, B. L. (1980) An enzymatic assay for β-hydroxybutyric acid in liquid whole egg, J. Sci. Food Agric. 31, 905–910.
- Riis, V., Mai, W. (1988) Gas chromatographic determination of poly-β-hydroxybutyric acid in microbial biomass after hydrochloric acid propanolysis, J. Chromatogr. 445, 285–289.
- Sanders, J., Hunter, B. (1993) Modern NMR-Spectroscopy: A Guide for Chemists, 2nd edition, Oxford: Oxford University Press.
- Satoh, H., Mino, T., Matsuo, T. (1992) Uptake of organic substrates and accumulation of polyhydroxyalkanoates linked with glycolysis of intracellular carbohydrates under anaerobic conditions in the biological excess phosphate removal process, Water Sci. Technol. 26, 933–942.
- Seebach, D., Fritz, M. G. (1999) Detection, synthesis, structure, and function of oligo(3-hydroxyalkanoates): contributions by synthetic organic chemists, Int. J. Biol. Macromol. 25, 217–236.
- Settle, F. A. (Ed.) (1997) Handbook of Instrumental Techniques for Analytical Chemistry, Upper Saddle River, NJ: Prentice-Hall.
- Silverstein, R. M., Webster, F. X. (1998) Spectrometric Identification of Organic Compounds, 6th edition, New York: John Wiley & Sons.
- Skoog, D. A. (1985) Principles of Instrumental Analysis, 3rd edition, Philadelphia, PA: CBS College Publishing.
- Slater, S., Gallaher, T., Dennis, D. (1992) Production of poly-(3-hydroxybutyrate-co-3-hydroxyvalerate) in a recombinant Escherichia coli strain, Appl. Environ. Microbiol. 58, 1089–1094.
- Slater, S., Houmiel, K., Tran, M., Mitsky, T., Taylor, N., Padgette, S., Gruys, K. (1998) Multiple β-ketothiolases mediate poly(β-hydroxyalkanoate) copolymer synthesis in Ralstonia eutropha, J. Bacteriol. 180, 1979–1987.
- Slepecky, R. A., Law, J. H. (1960) A rapid spectrophotometric assay of alpha, beta-unsaturated acids and beta-hydroxy acids, Anal. Chem. 32, 1697–1699.
- Snyder, L. R., Kirkland, J. J. (1996) Introduction to Modern Liquid Chromatography, 3rd edition, New York: John Wiley & Sons.
- Spyros, A., Argyropoulos, D. S., Marchessault, R. H. (1997) A study of poly(hydroxyalkanoate)s by quantitative 31P NMR spectroscopy: molecular weight and chain cleavage, Macromolecules 30, 327–329.
- Steinbüchel, A., Valentin, H. E. (1995) Diversity of bacterial polyhydroxyalkanoic acids, FEMS Microbiol. Lett. 128, 219–228.
- Sykes, P. (1986) A Guidebook to Mechanism in Organic Chemistry, Singapore: Longman Scientific & Technical.
- Takagi, Y., Hashii, M., Maehara, A., Yamane, T. (1999) Biosynthesis of polyhydroxyalkanoate with a thiophenoxy side group obtained from Pseudomonas putida, Macromolecules 32, 8315–8318.
- Timm, A., Steinbüchel, A. (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.
- Valentin, H. E., Schönebaum, A., Steinbüchel, A. (1992) Identification of 4-hydroxyvaleric acid as a constituent of biosynthetic polyhydroxyalkanoic acids from bacteria, Appl. Microbiol. Biotechnol. 36, 507–514.
- Valentin, H. E., Lee, E. Y., Choi, C. Y., Steinbüchel, A. (1994) Identification of 4-hydroxyhexanoic acid as a new constituent of biosynthetic polyhydroxyalkanoic acids from bacteria, Appl. Microbiol. Biotechnol. 40, 710–716.
- Valentin, H. E., Berger, P. A., Gruys, K. J., De Andrade Rodrigues, M. A., Steinbüchel, A., Tran, M., Asrar, J. (1999) Biosynthesis and characterization of poly(3-hydroxy-4-pentenoic acid), Macromolecules 32, 7389–7395.
- Wallen, L. L., Rohwedder, W. K. (1974) Poly-β-hydroxyalkanoate from activated sludge, Environ. Sci. Technol. 8, 576–579.
- Ward, A. C., Dawes, E. A. (1973) A disk assay for poly-β-hydroxybutyrate, Anal. Biochem. 52, 607–613.
- Williams, D. R., Anderson, A. J., Dawes, E. A., Ewing, D. F. (1994) Production of a co-polyester of 3-hydroxybutyric acid and 3-hydroxyvaleric acid from succinic acid by Rhodococcus ruber: biosynthetic considerations, Appl. Microbiol. Biotechnol. 40, 717–723.
- Williamson, D. H., Wilkinson, J. F. (1958) The isolation and estimation of poly-β-hydroxybutyrate inclusions of Bacillus species, J. Gen. Microbiol. 19, 198–209.
- Witholt, B., Huisman, G. W., Preusting, H (1990) Bacterial poly(3-hydroxyalkanoates), in: Novel Biosynthetic Biodegradable Polymers of Industrial Interest from Microorganisms ( A. E. Dawes, Ed.), Dordrecht: Kluwer, 161–173
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