Structure and Hydrolysis of Polyester Single Crystals
Part 3b. Polyesters
Dr. Tadahisa Iwata,
Prof. Dr. Yoshiharu Doi,
Dr. Tadahisa Iwata
- [email protected]
- +81-48-467-9586 | Fax: +81-48-462-4667
RIKEN Institute, Polymer Chemistry Laboratory, 2–1 Hirosawa, Wako-shi, Saitama, Japan, 351-0198
Search for more papers by this authorProf. Dr. Yoshiharu Doi
- [email protected]
- +81-48-467-9402 | Fax: +81-48-462-4667
RIKEN Institute, Polymer Chemistry Laboratory, 2–1 Hirosawa, Wako-shi, Saitama, Japan, 351-0198
Search for more papers by this authorDr. Tadahisa Iwata,
Prof. Dr. Yoshiharu Doi,
Dr. Tadahisa Iwata
- [email protected]
- +81-48-467-9586 | Fax: +81-48-462-4667
RIKEN Institute, Polymer Chemistry Laboratory, 2–1 Hirosawa, Wako-shi, Saitama, Japan, 351-0198
Search for more papers by this authorProf. Dr. Yoshiharu Doi
- [email protected]
- +81-48-467-9402 | Fax: +81-48-462-4667
RIKEN Institute, Polymer Chemistry Laboratory, 2–1 Hirosawa, Wako-shi, Saitama, Japan, 351-0198
Search for more papers by this authorFirst published: 15 January 2005
Abstract
- Introduction and Historical Outline
- Crystal Structure and Morphology
- Poly([R]-3-hydroxybutyrate)
- Poly([R]-3-hydroxybutyrate) copolymers
- Poly([R]-3-hydroxyvalerate)
- Poly(4-hydroxybutyrate)
- Poly(β-propiolactone)
- Poly(l-lactic acid)
- Poly(ɛ-caprolactone)
- Poly(ethylene succinate)
- Poly(ethylene adipate)
- Poly(tetramethylene succinate)
- Poly(tetramethylene adipate)
- Biodegradation of Single Crystals
- Poly([R]-3-hydroxybutyrate) and its Copolymers
- Poly(ethylene succinate)
- Poly(l-lactic acid)
- Other Aliphatic Polyesters and Chemical Hydrolyses
- Outlook and Perspectives
- Acknowledgements
References
- 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.
- Alper, R., Lundgren, D. G., Marchessault, R. H., Côté, W. A. (1963) Properties of poly-β-hydroxybutyrate. I. General considerations concerning the naturally occurring polymer, Biopolymers 1, 545–556.
- Anderson, A. J., Dawes, E. A. (1990) Occurrence, metabolism, metabolic role, and industrial uses of bacterial polyhydroxyalkanoates, Microbiol. Rev. 54, 450–472.
- Asahara, S., Katayama, S. (1966) Polymerization of β-propiolactone and structure of the resulting polymers, Kogyo Kagaku Zasshi (J. Chem. Soc. Jpn, Ind. Chem. Sect.) 69, 2179–2188.
- Barham, P. J., Keller, A., Otun, E. L., Holmes, P. A. (1984) Crystallization and morphology of a bacterial thermoplastic poly-3-hydroxybutyrate, J. Mater. Sci. 19, 2781–2794.
- Birley, C., Briddon, J., Sykes, K. E., Barker, P. A., Organ, S. J., Barham, P. J. (1995) Morphology of single-crystals of poly(hydroxybutyrate) and copolymers of hydroxybutyrate and hydroxyvalerate, J. Mater. Sci. 30, 633–638.
- Bittiger, H., Marchessault, R. H., Niewgisch, W. D. (1970) Crystal Structure of poly-ɛ-caprolactone, Acta Crystallogr. B26, 1923–1927.
- Bluhm, T. L., Hamer, G. K., Marchessault, R. H., Fyfe, C. A. (1986) Isodimorphism in bacterial poly(β-hydroxybutyrate-co-β-hydroxyvalerate), Macromolecules 19, 2871–2876.
- Brückner, S., Meille, S. V., Malpezzi, L., Cesaro, C., Navarini, L., Tombolini, R. (1988) The structure of poly(d-(–)-β-hydroxybutyrate). A refinement based on the Rietvelt method, Macromolecules 21, 967–972.
-
Bunn, C. W.
(1942)
Molecular structure and rubber-like elasticity. II. The stereochemistry of chain polymers,
Proc. Roy. Soc. A180,
67–81.
10.1098/rspa.1942.0025 Google Scholar
- Buléon, A., Chanzy, H. (1978) Single crystals of cellulose II, J. Polym. Sci.: Polym. Phys. Ed. 16, 833–839.
- Buléon, A., Chanzy, H. (1982) Single crystals of cellulose IVII: Influence of the cellulose molecular weight, J. Polym. Sci.: Polym. Phys. Ed. 20, 1081–1088.
- Chanzy, H., Excoffier, G., Guizard, C. (1981) Single crystals of dextran: high temperature polymorph, Carbohydr. Polym. 1, 67–77.
- Chanzy, H., Comtat, J., Dube, M., Marchessault, R. H. (1979) Enzymatic degradation of β(1→4)xylan single crystals, Biopolymers 18, 2459–2464.
- Chatani, Y., Okita, Y., Tadokoro, H., Yamashita, Y. (1970) Structural studies of polyesters. III. Crystal structure of poly-ɛ-capralactone, Polym. J. 1, 555–562.
- Cornibert, J., Marchessault, R. H. (1972) Physical properties of poly-β-hydroxybutyrate. IV. Conformational analysis and crystalline structure, J. Mol. Biol. 71, 735–756.
- Dawes, E. A., Senior, P. J. (1973) The role and regulation of energy reserve polymers in microorganisms, Adv. Microb. Physiol. 10, 135–266.
- De Santis, P., Kovacs, A. J. (1968) Molecular conformation of poly(S-lactic acid), Biopolymers 6, 299–306.
- Doi, Y. (1990) Microbial Polyesters, New York: VCH.
- Doi, Y., Kitamura, S., Abe, H. (1995) Microbial synthesis and characterization of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate), Macromolecules 28, 4822–4828.
- Eling, B., Gogolewski, S., Pennings, A. J. (1982) Biodegradable materials of poly(l-lactic acid). I. Melt-spun and solution-spun fibers, Polymer 23, 1587–1593.
- Fischer, E. W., Sterzel, H. J., Wegner, G. (1973) Investigation of structure of solution grown crystals of lactide copolymers by means of chemical-reactions, Kolloid-Z. Z. Polym. 251, 980–990.
- Fukuzaki, H., Yoshida, M., Asano, M., Kumakura, M. (1989) Synthesis of copoly(d,l-lactic acid) with relatively low-molecular weight and in vitro degradation, Eur. Polym. J. 25, 1019–1026.
- Fuller, C. S., Erickson, C. L. (1937) An X-ray study of some linear polyesters, J. Am. Chem. Soc. 59, 344–351.
- Fuller, C. S., Frosch, C. J. (1939) Further investigation of the chain structure of linear polyesters, J. Phys. Chem. 43, 323–334.
- Furuhashi, Y., Iwata, T., Sikorski, P., Atkins, E., Doi, Y. (2000) Structure and morphology of the aliphatic polyester poly-β-propiolactone in solution-grown chain-folded lamellar crystals, Macromolecules 33, 9423–9431.
- Gilkes, N. R., Henrissat, B., Kilburn, D. G., Miller, R. C., Warren, R. A. J. (1991) Domains in microbial β-1,4-glycanases: sequence conservation, function, and enzyme families, Microbiol. Rev. 55, 303–315.
- Haywood, G. W., Anderson, A. J., Williams, D. R., Dawes, E. A., Ewing, D. F. (1991) Accumulation of a poly(hydroxyalkanoate) copolymer containing primarily 3-hydroxyvalearate from simple carbohydrate substrates by Rhodococcus sp. Nicimb 4012, Int. J. Biol. Macromol. 13, 83–88.
- Hocking, P. J., Marchessault, R. H., Timmins, M. R., Lenz, R. W., Fuller, R. C. (1996) Enzymatic degradation of single crystals of bacterial and synthetic poly(β-hydroxybutyrate), Macromolecules 29, 2472–2478.
-
Holmes, P. A.
(1988)
Biologically produced (R)-3-hydroxyalkanoate polymers and copolymers, in: Developments in Crystalline Polymers 2 ( D. C. Bassett, Ed.), New York: Elsevier Applied Science,
1–65.
10.1007/978-94-009-1341-7_1 Google Scholar
- Hoogsteen, W., Postema, A. R., Pennings, A. J., Tenbrinke, G., Zugenmaier, P. (1990) Crystal-structure, conformation, and morphology of solution-spun poly(l-lactide) fibers, Macromolecules 23, 634–642.
- Hu, H. L., Dorset, D. L. (1990) Crystal-structure of poly(ɛ-caprolactone), Macromolecules 23, 4604–4607.
- Ichikawa, Y., Suzuki, J., Washiyama, J., Moteki, Y., Noguchi, K., Okuyama, K. (1994) Strain-induced crystal modification in poly(tetramethylene succinate), Polymer 35, 3338–3339.
- Ichikawa, Y., Washiyama, J., Moteki, Y., Noguchi, K., Okuyama, K. (1995) Crystal transition mechanisms in poly(tetramethylene succinate), Polymer J. 27, 1230–1238.
- Ichikawa, Y., Kondo, H., Igarashi, Y., Noguchi, K., Okuyama, K., Washiyama, J. (2000) Crystal structure of α and β forms of poly(tetramethylene succinate), Polymer 41, 4719–4727.
- Ihn, K. J., Yoo, E. S., Im, S. S. (1995) Structure and morphology of poly(tetramethylene succinate) crystals, Macromolecules 28, 2460–2464.
- Imberty, A., Chanzy, H., Pérez, S., Buléon, A., Tran, V. (1987) New three-dimensional structure for A-type starch, Macromolecules 20, 2634–2636.
- Iwata, T., Okamura, K., Azuma, J., Tanaka, F., Chanzy, H. (1994) Single crystals of regio-selectively substituted cellulose hetero-esters, Cellulose 1, 67–76.
- Iwata, T., Doi, Y., Kasuya, K., Inoue, Y. (1997a) Visualization of enzymatic degradation of poly[(R)-3-hydroxybutyrate] single crystals by an extracellular PHB depolymerase, Macromolecules 30, 833–839.
- Iwata, T., Doi, Y., Tanaka, T., Akehata, T., Shiromo, M., Teramachi, S. (1997b) 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.
- Iwata, T., Doi, Y. (1998) Morphology and enzymatic degradation of poly(l-lactic acid) single crystals, Macromolecules 31, 2461–2467.
- Iwata, T., Doi, Y., Nakayama, S., Sasatsuki, H., Teramachi, S. (1999a) Structure and enzymatic degradation of poly(3-hydroxybutyrate) copolymer single crystals with an extracellular PHB depolymerase from Alcaligenes faecalis T1, Int. J. Biol. Macromol. 25, 169–176.
- Iwata, T., Doi, Y., Kokubu, F., Teramachi, S. (1999b) Alkaline hydrolysis of solution-grown poly[(R)-3-hydroxybutyrate] single crystals, Macromolecules 32, 8325–8330.
-
Iwata, T.,
Doi, Y.
(1999)
Crystal structure and biodegradation of aliphatic polyester crystals,
Macromol. Chem. Phys. 200,
2429–2442.
10.1002/(SICI)1521-3935(19991101)200:11<2429::AID-MACP2429>3.0.CO;2-# CAS Web of Science® Google Scholar
- Iwata, T., Doi, Y. (2000) Morphology and crystal structure of solution-grown single crystals of poly[(R)-3-hydroxyvalerate], Macromolecules 33, 5559–5565.
- Iwata, T., Doi, Y., Isono, K., Yoshida, Y. (2000) Crystal structure and enzymatic degradation of poly(ethylene succinate) single crystals, Polym. Prepr., Jpn. 49, 1012.
- Iwata, T., Doi, Y. (2001) Alkaline-hydrolysis of solution-grown poly(L-lactic acid) single crystals, Sen-i Gakkai-shi 57, 172–177.
- Jaccodine, R. (1955) Observation of spiral growth steps in ethylene polymer, Nature 176, 305–306.
- Jackanicz, T. M., Nash, H. A., Wise, D. L., Gregory, J. B. (1973) Polylactic acid as a biodegradable carrier for contraceptive steroids, Contraception 8, 227–234.
- Jamshidi, K., Eberhart, R. C., Hyon, S.-H., Ikada, Y. (1987) Characterization of polylactide synthesis, Polym. Prepr. 28, 236–237.
- Kalb, B., Pennings, A. J. (1980) General crystallization behavior of poly(l-lactic acid), Polymer 21, 607–612.
- Kamiya, N., Sakurai, M., Inoue, Y., Chujo, R., Doi, Y. (1991) Studies of cocrystallization of poly(3-hydroxybutyrate-co-3-hydroxyvalerate) by solid-state high-resolution 13C-NMR spectroscopy and differential scanning calorimetry, Macromolecules 24, 2178–2182.
- Kasuya, K., Inoue, Y., Tanaka, T., Akehata, T., Iwata, T., Fukui, T., Doi, Y. (1997) Biochemical and molecular characterization of the polyhydroxybutyrate depolymerase of Comamonas acidovorans YM1609, isolated from freshwater, Appl. Environ. Microbiol. 63, 4844–4852.
- Kasuya, K., Ohura, T., Msuda, K., Doi, Y. (1999) Substrate and binding specificities of bacterial polyhydroxybutyrate depolymerases, Int. J. Biol. Macromol. 24, 329–336.
- Keller, A. (1957) A note on single crystals in polymers: Evidence for a folded chain configuration, Phil. Mag. 2, 1171.
- Kellett, L. E., Poole, D. M., Ferreira, L. M. A., Durrant, A. J., Hazlewood, G. P., Gilbert, H. J. (1990) Xylanase B and an arabinofuranosidase from Pseudomonas fluorescens subsp. cellulosa contain identical cellulose-binding domains and are encoded by adjacent genes, Biochemical J. 272, 369–376.
- Khoury, F., Padden, Jr., F. J. (1960) On the growth habit of twinned crystals of polyethylene, J. Polym. Sci. 47, 455–468.
- Kleine, V. J., Kleine, H.-H. (1959) Über hochmolekular, insbesondere optisch aktive polyester der milchsäure, ein beitrag zur stereochemie makromolekularer verbindungen, Makromol. Chem. 30, 23–38.
- Kobayashi, J., Asahi, T., Ichiki, M., Oikawa, A., Suzuki, H., Watanabe, T., Fukada, E., Shikinami, Y. (1995) Structural and optical-properties of poly(lactic acids), J. Appl. Phys. 77, 2957–2973.
- Kobayashi, S., Kogure, K., Mitomo, H., Doi, Y. (1998) Crystal structure of poly(4-hydroxybutyrate), Polym. Prepr., Jpn. 47, 968.
- Kojima, T., Nakano, M., Juni, K., Inoue, S., Yoshida, Y. (1984) Preparation and evaluation of polycarbonate microspheres containing local-anesthetics, Chem. Pharm. Bull. 32, 2795–2802.
- Kulkarni, R. K., Moore, E. G., Hegyeli, A. F., Leonard, F. (1971) Biodegradable poly(lactic acid) polymers, J. Biomed. Mater. Res. 5, 169–181.
- Kumagai, Y., Kanesawa, Y., Doi, Y. (1992) Enzymatic degradation of microbial poly(3-hydroxybutyrate) films, Makromol. Chem. 193, 53–57.
- 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.
- Lee, W.-K., Iwata, T., Abe, H., Doi, Y. (2000) Studies on the enzymatic degradation of solution-grown lamellar crystals of poly[(R)-3-hydroxybutyrate]: Defects in crystals, Macromolecules 33, 9535–9541.
- Leenslag, J. W., Pennings, A. J. (1987a) Synthesis of high-molecular-weight poly(l-lactide) initiated with tin 2–ethylhexanoate, Macromol. Chem. 188, 1809–1814.
- Leenslag, J. W., Pennings, A. J., Bos, R. R. M., Rozema, F. R., Boering, G. (1987b) Resorbable materials of poly(l-lactide). VII, In vivo and in vitro degradation, Biomaterials 8, 311–314.
- Lemoignei, M. (1926) Produit de déhydratation et de polymeerisation de l'acid β-oxybutyrique, Bull. Soc. Chim. Biol. 8, 770–782.
- Lemoignei, M. (1927) Etudes sur l'autolyse microbiènne origine de l'acid β-oxybutyrique formé par autolyse, Ann. Inst. Pasteur 41, 148–165.
- Lundgren, D. G., Alper, R., Schnaitman, C., Marchessault, R. H. (1965) Characterization of poly-β-hydroxybutyrate extracted from different bacteria, J. Bacteriol. 89, 245–251.
- Lusty, C. J., Doudoroff, M. (1966) Poly-β-hydroxybutyrate depolymerase of Pseudomonas lemoignei, Proc. Natl. Acad. Sci. USA 56, 960–965.
- Makino, K., Arakawa, M., Kondo, T. (1985) Preparation and in vitro degradation properties of polylactide microcapsules, Chem. Pharm. Bull. 33, 1195–1201.
- Marchessault, R. H., Revol, J. F., Bobitt, T. F., Nordin, J. H. (1980a) Enzymatic depolymerization of lamellar single crystals of nigeran, Biopolymers 19, 1069–1080.
- Marchessault, R. H., Bleha, T., Deslandes, Y., Revol, J.-F. (1980b) Conformation and crystalline structure of (2→1)-β-D-fructofuranan (inulin), Can. J. Chem. 58, 2415–2422.
- Marchessault, R. H., Coulombe, S., Morikawa, H., Okamura, K., Revol, J. F. (1981) Solid-state properties of poly-β-hydroxybutyrate and of its oligomers, Can. J. Chem. 59, 38–44.
- Marchessault, R. H., Morehead, F. F., Walter, N. M., Glaudemans, C. P. J. (1961) Morphology of xylan single crystals, J. Polym. Sci. 51, S66–S68.
- Marchessault, R. H., Morikawa, H., Revol, J. F., Bluhm, T. L. (1984) Physical properties of a naturally occurring polyester: poly(β-hydroxyvalerate) and poly(β-hydroxybutyrate), Macromolecules 17, 1882–1884.
- Marchessault, R. H., Bluhm, T. L., Deslands, Y., Hamer, G. K., Orts, W. J., Sundararajan, P. R., Taylor, M. G., Bloembergen, S., Holden, D. A. (1988) Poly(β-hydroxyalkanoates)–biorefinery polymers in search of applications, Makromol. Chem., Macromol. Symp. 19, 235–254.
- Marchessault, R., Debzi, E., Revol, J., Steinbüchel, A. (1995) Single crystals of bacterial and synthetic poly(3-hydroxyvalerate), Can. J. Microbiol. 41 (Suppl. 1), 297–302.
- Mike, R., Blackwell, J. (1979) Polymorphic structures of poly(tetramethylene adipate), J. Macromol. Sci.-Phys. B16, 407–417.
- Mitomo, H., Barham, P. J., Keller, A. (1987) Crystallization and morphology of poly(β-hydroxybutyrate) and its copolymer, Polym. J. 19, 1241–1253.
- Mitomo, H., Kobayashi, S., Morishita, N., Doi, Y. (1995) Structural changes and properties of P(3HB-co-4HB), Polymer Prepr., Jpn 44, 3156–3157.
- Miyata, T., Masuko, T. (1997) Morphology of poly(l-lactide) solution-grown crystals, Polymer 38, 4003–4009.
- Mukai, K., Yamada, K., Doi, Y. (1993) Enzymatic degradation of poly(hydroxyalkanoates) by a marine bacterium, Polym. Degrad. Stab. 41, 85–91.
- Mukai, K., Yamada, K., Doi, Y. (1994) Efficient hydrolysis of polyhydroxyalkanoates by Pseudomonas stutzeri YM1414 isolated from lake water, Polym. Degrad. Stab. 43, 319–327.
- Müller, B., Jendrossek, D. (1993) Purification and properties of poly(3-hydroxyvaleric acid) depolymerase from Psedomonas lemoignei, Appl. Microbiol. Biotechnol. 38, 487–492.
- Murase, T., Iwata, T., Doi, Y. Direct observation of enzymatic degradation behavior of poly[ (R)-3-hydroxybutyrate] lamellar single crystals by atomic force microscopy, Macromolecules, in press.
- Nakamura, S., Doi, Y., Scandola, M. (1992) Microbial synthesis and characterization of poly(3-hydroxybutyrate-co-4-hydroxybutyrate), Macromolecules 25, 4237–4241.
- Nobes, G. A. R., Marchessault, R. H., Chanzy, H., Briese, B. H., Jendrossek, D. (1996) Splintering of poly(3-hydroxybutyrate) single crystals by a PHB-depolymerase from Pseudomonas lemoignei, Macromolecules 29, 8330–8333.
- Nobes, G. A. R., Marchessault, R. H., Briese, B. H., Jendrossek, D. (1998) Microscopic visualization of the enzymatic degradation of poly(3HB-co-3HV) and poly(3HV) single crystals by PHA depolymerases from Pseudomonas lemoignei, J. Environ. Polym. Degrad. 6, 99–107.
- Ohura, T., Kasuya, K., Doi, Y. (1999) Cloning and characterization of the polyhydroxybutyrate depolymerase gene of Pseudomonas stutzeri and analysis of the function of substrate-binding domains, Appl. Environ. Microbiol. 65, 189–197.
-
Okamura, K.,
Marchessault, R. H.
(1967)
X-ray structure of poly-β-hydroxybutyrate, in: Conformation of Biopolymers ( G. N. Ramachandran, Ed.) New York: Academic Press,
709–720, Vol. 2.
10.1016/B978-1-4832-2843-3.50023-6 Google Scholar
- Okamura, S., Hayashi, T., Kitanishi, Y. (1962a) Radiation-induced solid-state polymerization of ring compounds, J. Polym. Sci. 58, 925–953.
- Okamura, S., Higashimura, T., Tanaka, A., Kato, R., Kikuchi, Y. (1962b) Infra-red adsorption spectrum of poly-β-propiolactone obtained by two kinds of ionic polymerization, Macromol. Chem. 54, 226–229.
- Pazur, R. J., Hocking, P. J., Raymond, S., Marchessault, R. H. (1998a) Crystal structure of syndiotactic poly(β-hydroxybutyrate) from X-ray fiber and powder diffraction analyses and molecular modeling, Macromolecules 31, 6585–6592
- Pazur, R. J., Raymond, S., Hocking, P. J., Marchessault, R. H. (1998b) Molecular modeling of helical and extended-chain polyhydroxybutyrates and polytetramethylene succinate, Polymer 39, 3065–3072.
- Penning, J. P., Dijkstra, H., Pennings, A. J. (1993) Preparation and properties of absorbable fibers from l-lactide copolymers, Polymer 34, 942–951.
- Pizzoli, M., Scandola, M., Ceccorulli, G. (1994) Crystallization kinetics and morphology of poly(3-hydroxybutyrate) cellulose ester blends, Macromolecules 27, 4755–4761.
- Reeve, M. S., McCarthy, S. P., Downey, M. J., Gross, R. A. (1994) Polylactide stereochemistry: effect on enzymatic degradability, Macromolecules 27, 825–831.
- Reneker, D. H., Geil, P. H. (1960) Morphology of polymer single crystals, J. Appl. Phys. 31, 1916–1925.
- Revol, J. F., Chanzy, H., Deslandes, Y., Marchessault, R. H. (1989) High resolution electron microscopy of poly(β-hydroxybutyrate), Polymer 30, 1973–1976.
- Roche, E., Chanzy, H., Boudeulle, M., Marchessault, R. H., Sundararajan, P. (1978) Three-dimensional crystalline structure of cellulose triacetate II, Macromolecules 11, 86–94.
- Saito, T., Suzuki, K., Ymamoto, J., Fukui, T., Miwa, K., Tomita, K., Nakanishi, S., Odani, S., Suzuki, J., Ishikawa, K. (1989) Cloning, nucleotide-sequence, and expression in Escherichia coli of the gene for poly(3-hydroxybutyrate) depolymerase from Alcaligenes faecalis, J. Bacteriol. 171, 184–189.
- Sauer, J. A., Morrow, D. R., Richardson, G. C. (1965) Morphology of solution-grown polypropylene crystal aggregates, J. Appl. Phys. 36, 3017–3021.
- Scandla, M., Ceccorulli, G., Pizzoli, M. (1992) Miscibility of bacterial poly(3-hydroxybutyrate) with cellulose esters, Macromolecules 25, 6441–6446.
- Schlesinger, W., Leeper, H. M. (1953) Gutta. I. Single crystals of alpha-gutta, J. Polym. Sci. 11, 203–213.
- Seebach, D., Burger, H. M., Muller, H. M., Lengweiler, U. D., Beck, A. K., Sykes, K. E., Barker, P. A., Barham, P. J. (1994) Synthesis of linear oligomers of (R)-3-hydroxybutyrate and solid-state structural investigations by electron microscopy and X-ray scattering, Helv. Chim. Acta 77, 1099–1123.
- Shimamura, E., Kasuya, K., Kobayashi, G., Shiotani, T., Shima, Y., Doi, Y. (1994) Physical properties and biodegradability of microbial poly(3-hydroxybutyrate-co-3-hydroxyhexanoate), Macromolecules 27, 878–880.
- Shinomiya, M., Iwata, T., Kasuya, K., Doi, Y. (1997) Cloning of the gene for poly(3-hydroxybutyric acid) depolymerase of Comamonas testosteroni and functional analysis of its substrate-binding domain, FEMS Microbiol. Lett. 154, 89–94.
- Shinomiya, M., Iwata, T., Doi, Y. (1998) The adsorption of substrate-binding domain of PHB depolymerases to the surface of poly(3-hydroxybutyric acid), Int. J. Biol. Macromol. 22, 129–135.
- Shuto, Y., Okamura, K., Azuma, J., Tanaka, F., Chanzy, H. (1989) X-ray and electron diffraction study of some cellulose derivatives, in: Cellulose: Structural and Functional Aspects ( J. F. Kennedy, G. O. Phillips, P. A. Williams, Eds.), Chichester: Ellis Horwood, 283–288,
- Sipos, L., Zsuga, M., Kelen, T. (1992) Living ring-opening polymerization of l,l-lactide initiated with potassium tert-butoxide and its 18-crown-6 complex, Polym. Bull. 27, 495–502.
- Spyros, A., Marchessault, R. H. (1995) 13C Nuclear magnetic relaxation measurement of poly(4-hydroxybutyrate) and poly(3-hydroxybutyrate-co-4-hydroxybutyrate) in the bulk, Macromolecules 28, 6108–6111.
- Steinbüchel, A., Debzi, E., Marchessault, R. H., Timm, A. (1993) Synthesis and production of poly(3-hydroxyvaleric acid) homopolyester by Chromobacterium violaceum, Appl. Microbiol. Biotechnol. 39, 443–449.
- Sudesh, K., Fukui, T., Doi, Y. (1998) Genetic analysis of Comamonas acidovorans polyhydroxyalkanoate synthase and factors affecting the incorporation of 4-hydroxybutyrate monomer, Appl. Environ. Microbial. 64, 3437–3443.
- Suehiro, K., Chatani, Y., Tadokoro, H. (1975) Structural studies of polyesters. VI. Disordered crystal structure (Form II) of poly(β-propiolactone), Polym. J. 7, 352–358.
- Sykes, K. E, McMaster, T. J., Miles, M. J., Barker, P. A., Barham, P. J., Seebach, D., Muller, H. M., Lengweiler, U. D. (1995) Direct imaging of the surfaces of poly(β-hydroxybutyrate) and hydroxybutyrate oligomers by atomic force microscopy, J. Mater. Sci. 30, 623–627.
- Sykes, K. E., Barham, P. J., Hobbs, J. K., Fuljames, C., Debouzy, I., Baker, A. A., McMaster, T. J., Miles, M. J., Jackson, R., Farrell, R., Gross, R. A. (1997) Degradation studies of single crystals of poly(hydroxybutyrate), in: 1996 International Symposium on Bacterial Polyhydroxyalkanoates ( G. Eggink, A. Steinbüchel, Y. Poirier, B. Witholt, Eds.), Ottawa: NRC Research Press, 66–77.
- Tanio, T., Fukui, T., Shirakura, Y., Saito, T., Tomita, K., Kaiho, T., Masamune, S. (1982) An extracellular poly(3-hydroxybutyrate) depolymerase from Alcaligenes faecalis, Eur. J. Biochem. 124, 71–77.
- Tomasi, G., Scandola, M., Briese, B. H., Jendrossek, D. (1996) Enzymatic degradation of bacterial poly(3-hydroxybutyrate) by a depolymerase from Pseudomonas lemoignei, Macromolecules 29, 507–513.
- Turner-Jones, A., Bunn, C. W. (1962) The crystal structures of polyethylene adipate and polyethylene suberate, Acta Crystallogr. 15, 105–113.
- Ueda, A. S., Chatani, Y., Tadokoro, H. (1971) Structural Studies of polyesters. IV. Molecular and crystal structures of poly(ethylene succinate) and poly(ethylene oxalate), Polym. J. 2, 387–397.
- Vainionpää, S., Rokkanen, P., Törmälä, P. (1989) Surgical application of biodegradable polymers in human-tissues, Prog. Polym. Sci. 14, 679–716.
- VanderHart, D. L., Orts, W. J., Marchssault, R. H. (1995) 13C NMR Determination of the degree of cocrystallization in random copolymers of poly(β-hydroxybutyrate-co-betahydroxyvalerate), Macromolecules 28, 6394–6400.
- Wasai, T., Saegusa, T., Furukawa, J. (1964) Molecular structure of poly-β-propiolactone, Kogyo Kagaku Zasshi (J. Chem. Soc. Jpn, Ind. Chem. Sect.) 67, 601–604.
- Watanabe, T., Suzuki, K., Oyanagi, W., Ohnishi, K., Tanaka, H. (1990) Gene cloning of chitinase-A1 from Bacillus circulans WL-12 revealed its evolutionary relationship to serratia chitinase and to the type-III homology units of fibronectin, J. Biol. Chem. 265, 15659–15665.
- Welland, E. L., Stejny, J., Halter, A., Keller, A. (1989) Selective degradation of chain folded single-crystals of poly(β-hydroxybutyrate), Polym. Commun. 30, 302–304.
-
Williams, D. F.
(1981)
Enzymatic hydrolysis of polylactic acid,
Eng. Med. 10,
5–7.
10.1243/EMED_JOUR_1981_010_004_02 Google Scholar
- Yamada, K., Mukai, K., Doi, Y. (1993) Enzymatic degradation of poly(hydroxyalkanoates) by Pseudomonas pickettii, Int. J. Biol. Macromol. 15, 215–220.
- Yokouchi, M., Chatani, Y., Tadokoro, H., Teranishi, K., Tani, H. (1973) Structural studies of polyesters. V. Molecular and crystal structures of optically active and racemic poly(β-hydroxybutyrate), Polymer 14, 267–272.
- Yokouchi, M., Chatani, Y., Tadokoro, H., Tani, H. (1974) Structural studies of polyesters. VII. Molecular and crystal-structures of racemic poly(β-ethyl-β-propiolactone), Polym. J. 6, 248–255.
- Yoo, E. S., Im, S. S. (1998) Morphological study on hydrolytic degradation of poly(tetramethylene succinate) single crystals and spherulites, J. Environ. Polym. Degrad. 6, 223–231.
- Yoshie, N., Sakurai, M., Inoue, Y., Chujo, R. (1992) Cocrystallization of isothermally crystallized poly(3-hydroxybutyrate-co-3-hydroxyvalerate), Macromolecules 25, 2046–2048.
- Zugenmaier, P. (1983) Structural investigations on cellulose derivatives, J. Appl. Polym. Sci.: Appl. Polym. Symp. 37, 223–238.
Biopolymers Online: Biology • Chemistry • Biotechnology • Applications
Browse other articles of this reference work: