Poly(β-hydroxybutyrate) stereoisomers: a model study of the effects of stereochemical and morphological variables on polymer biological degradability

Kemnitzer, John E.; McCarthy, Stephen P.; Gross, Richard A.

doi:10.1021/ma00048a011

Cited by 107 publications

(83 citation statements)

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“…Considering these problems, biodegradable plastics have been the subject of many research papers. Several kinds have been produced, such as poly (b-hydroxybutyrate), polycaprolactone, and polyglycolic acid, and depolymerases capable of degrading these materials have been reported (Benedict et al, 1983;Chu, 1981;Kemnitzer et al, 1992;Reeve et al, 1994;Tanino et al, 1982). Poly-(L-lactide) (PLA), one of these biodegradable plastics, however, is expected to be used widely since its cost has decreased recently; already it is used in the medical field (Leenslag et al, 1987;Penning et al, 1993).…”

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confidence: 99%

Isolation of a microorganism capable of degrading poly-(L-lactide).

Ikura

Kudo

1999

J. Gen. Appl. Microbiol.

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Plastics are beneficial because of their facility, lightness, ease in processing, transparency, and low cost. Although some plastics are reused and recycled, the disposal of a large quantity of used plastic waste poses a great problem. Spacious land is required for burying waste material, and poisonous gas is often emitted when plastic waste is incinerated. Furthermore, abiotic plastics spoil the scenery and the ecological systems of many forms of life. Considering these problems, biodegradable plastics have been the subject of many research papers. Several kinds have been produced, such as poly (b-hydroxybutyrate), polycaprolactone, and polyglycolic acid, and depolymerases capable of degrading these materials have been reported (Benedict et al., 1983;Chu, 1981;Kemnitzer et al., 1992;Reeve et al., 1994;Tanino et al., 1982). Poly-(L-lactide) (PLA), one of these biodegradable plastics, however, is expected to be used widely since its cost has decreased recently; already it is used in the medical field (Leenslag et al., 1987;Penning et al., 1993). PLA and other lactic acid-containing polymers are synthesized chemically (Dubois et al., 1991;Kricheldorf et al., 1992;Penning et al., 1993). Apart from its biodegradability, PLA has attracted attention as a material that can be made from renewable resources such as starch because lactic acid is produced through the fermentation of starch or glucose. It is completely harmless compared with abiotic polymers when used in vessels for edible products. PLA is known to degrade slowly in natural soil, but it takes a long time for degradation to start. It can be hydrolyzed enzymatically (Ebeling et al., 1974;Fukuzaki et al., 1989;Reeve et al., 1994). Nevertheless, only a few reports have been made so far on the direct degradation of PLA by microorganisms.One report concerns a mold capable of assimilating soluble PLA-oligomer and PLA-copolymer with glycerol (Torres et al., 1996). Furthermore, Pranamuda et al. (1997) reported the degradation of PLA by Amycolatopsis sp.In the present study, we isolated a microorganism capable of efficiently degrading homo-PLA film in liquid culture. This strain differs from the one reported by Pranamuda et al. (1997), especially in terms of growth temperature and spore formation. In this report, we describe the identification of the PLA-degrading organism, the PLA-degradation conditions, and the products found in the culture supernatant. Materials and Methods Medium Isolation of a microorganism capable of degrading poly-(L-lactide)Yoko Ikura* and Toshiaki KudoInstitute of Physical and Chemical Research ( RIKEN ), Wako 351-0198, Japan (Received February 1, 1999; Accepted October 19, 1999) The isolation of poly-(L-lactide) (PLA)-degrading microorganisms was investigated. A PLA-degrading actinomycete, strain No. 3118, was isolated and tentatively identified as a member of the genus Amycolatopsis. The optimum conditions for degradation of PLA were 43°C at about pH 7 in a mineral salt medium with a low concentration of organic nutrients (0.002% yea...

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confidence: 99%

Isolation of a microorganism capable of degrading poly-(L-lactide).

Ikura

Kudo

1999

J. Gen. Appl. Microbiol.

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“…The syn-PHB polymer was successfully synthesized using the procedure as detailed by Kemnitzer et al (1992) with minor modifications. The finished product is in powder form and has M w 1.5×10 5 , M w /M n 1.74 (also see Table 1) and racemic diad 0.62.…”

Section: Resultsmentioning

confidence: 99%

“…Previous investigation concluded that PHB degradation is soil dependent and degradation rate is generally higher in acidic soils than calcareous ones (Barak et al, 1991;Mergaert et al, 1993). syn-PHB was previously shown to be hydrolyzable by extracellular enzymes of Penicillium funiculosum (Kemnitzer et al, 1992) and by aqueous water (Doi,1990). Bacterial PHBs were previously reported to be degraded in thermophilic composting (Gilmore et al, 1992), soil (Barak et al, 1991;Mergaert et al, 1993), marine (Wirsen and Jannasch, 1993) and sewage sludge (Budwill et al, 1992).…”

Section: Resultsmentioning

confidence: 99%

“…The polymer syn-PHB was synthesized in bulk using a modified procedure as described by Kemnitzer et al (1992). The synthesis processes involved tri-n-butyltin methoxide (Sn(n-Bu) 3 OCH 3 ) to catalyze the ring-opening polymerization of racemic β-butyrolactone (BL) to form poly (β-hydroxybutyraye) (PHB) with syndiotactic (syn) placement.…”

Section: Synthesis Of Syn-phbmentioning

confidence: 99%

“…The weight loss was calculated as the difference in weight changes between initial and the sampling and expressed as mg mm −2 . Then, the samples were used for polymer molecular weight analysis using gel permeation chromatography as described early (Gu et al, 1994). The specimens were dissolved in chloroform (0.3%, w/v) and then 125 µL were used in analysis.…”

Section: Polymer Analysismentioning

confidence: 99%

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Biodegradability of chemically synthesized syndiotactic poly(β-[R]- hydroxybutyrate) in soil of Northeast China

Zhang

2017

Appl Env Biotechnol

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Degradability of syndiotactic poly ([R]-β-hydroxybutyrate) (syn-PHB), a chemically synthesized PHB, was investigated in this study by incubation of the polymer films in a soil of northeastern China. During incubation, progressive weight loss of the syn-PHB films and a corresponding decrease of molecular weight were observed over the 90 days of incubation indicating the biodegradation of syn-PHB and a random cleavage of the ester bonds. Microorganisms isolated and identified from the partially degraded films included Pseudomonas spp., Alcaligenese sp., and Comamonas sp.. Our results suggest that chemically synthesized syn-PHB is biodegradable under aerobic conditions in soil.

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Polymerization of β-Butyrolactone Initiated withAl(OiPr)3

1996

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Polymerization of β‐butyrolactone has been studied in toluene with Al(OiPr)3 as an initiator. The ring‐opening polyaddition proceeds through a coordination–insertion mechanism at a very low rate. Well defined α‐isopropylester, ω‐hydroxy poly(β‐butyrolactone)s (PBL) are formed with a narrow molecular weight distribution at low monomer‐to‐initiator molar ratios, When this ratio is higher (ca. 170), a competition occurs between propagation and side reactions, i.e. elimination, inter‐ and intra‐molecular transesterifications and thermal degradation, which is responsible for a loss of control of the PBL molecular charcteristics. The addition of a Lewis base (1 equivalent of nicotine/Al) to the Al‐alkoxide initiator has no significant effect on the polymerization rate, although the chain microstructure is deeply affected since predominantly syndiotactic PBL chains are formed (63% syndio‐diads) in contrast to a completely atactic polymer in the absence of nicotine.

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Poly(β-hydroxybutyrate) stereoisomers: a model study of the effects of stereochemical and morphological variables on polymer biological degradability

Cited by 107 publications

References 6 publications

Isolation of a microorganism capable of degrading poly-(L-lactide).

Isolation of a microorganism capable of degrading poly-(L-lactide).

Biodegradability of chemically synthesized syndiotactic poly(β-[R]- hydroxybutyrate) in soil of Northeast China

Polymerization of β-Butyrolactone Initiated withAl(OiPr)3

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