Lipase-Catalyzed Transformation of Unnatural-Type Poly(3-hydroxybutanoate) into Reactive Cyclic Oligomer

Osanai, Yasushi; Toshima, Kazunobu; Yoshie, Naoko; Inoue, Yoshio; Matsumura, Shuichi

doi:10.1002/1616-5195(20020201)2:2<88::aid-mabi88>3.0.co;2-5

Cited by 11 publications

(20 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It was confirmed that almost all fractions of the degradation products were of the cyclic form and no linear oligomers having a molecular mass of 18 Da higher than that of the corresponding cyclic oligomer were detected as measured by MALDI‐TOF MS. Similar results were obtained for the lipase‐catalyzed degradation of PCL, PBA, PHB and poly(trimethylene carbonate), such that the macrocycles were produced as the degradation products 4–13. The enzyme concentration significantly influenced both the molecular weight of the oligomer and the oligomer yield.…”

Section: Resultssupporting

confidence: 72%

“…However, the enzymatic degradation of poly(lactic acid) was exclusively carried out using proteinase K in a buffer solution as a convenient evaluation of biodegradability. We reported the selective degradative transformation into repolymerizable oligomers and repolymerization with respect to the AB type polymers, such as poly( ε ‐caprolactone) (PCL) and poly(3‐hydroxybutanoate) (PHB), and AA‐BB type polymers, such as poly(butylene adipate) (PBA) and poly(trimethylene carbonate), by lipase in both an organic solvent and supercritical carbon dioxide fluid 4–13. However, the transformation of the poly(lactic acid) into a cyclic oligomer has not yet been reported.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Lipase‐Catalyzed Transformation of Poly(lactic acid) into Cyclic Oligomers

Takahashi

Okajima

Toshima

et al. 2004

Macromolecular Bioscience

Self Cite

View full text Add to dashboard Cite

Enzymatic transformations into cyclic oligomers were carried out with the objective of developing chemical recycling of poly(lactic acid)s, such as poly(D,L-lactic acid) (PDLLA), poly(D-lactic acid) (PDLA) and poly(L-lactic acid) (PLLA), which are typical biodegradable polymers. They were degraded by lipase in an organic solvent to produce the corresponding cyclic oligomer with a molecular weight of several hundreds. PDLLA (with a Mw of 84,000) was quantitatively transformed into cyclic oligomers by lipase RM (Lipozyme RM IM) in chloroform/hexane at 60 degrees C. PLLA (with a Mw of 120,000) was transformed into cyclic oligomer by lipase CA (Novozym 435) at a higher temperature of 100 degrees C in o-xylene. The oligomer structure was identified by 1H and 13C NMR spectroscopy and MALDI-TOF (matrix assisted laser desorption/ionization-time-of-flight) mass spectrometry.

show abstract

Section: Resultssupporting

confidence: 72%

Section: Introductionmentioning

confidence: 99%

Lipase‐Catalyzed Transformation of Poly(lactic acid) into Cyclic Oligomers

Takahashi

Okajima

Toshima

et al. 2004

Macromolecular Bioscience

Self Cite

View full text Add to dashboard Cite

show abstract

“…[128] Figure 7 shows the MALDI-TOF MS of the degradation products of syndiotactic (RS)-P(3HB) in toluene using lipase CA. [128] The degradation products were mainly composed of the cyclic forms as shown in this figure. The (RS)-P(3HB) is biodegraded to produce CO 2 and H 2 O.…”

Section: A New Route To Sustainable Chemical Recycling Ofmentioning

confidence: 44%

Enzyme-Catalyzed Synthesis and Chemical Recycling of Polyesters

Matsumura¹

2002

Macromol. Biosci.

Self Cite

113

View full text Add to dashboard Cite

This article summarizes the enzyme‐catalyzed synthesis and chemical recycling of biodegradable aliphatic polyesters and poly(carbonate ester)s directed towards establishing green polymer chemistry. Lipase catalyzes the condensation polymerization of a hydroxy acid, diacid with diol, diacid anhydride with oxirane, and polyanhydride with diol, or the ring‐opening polymerization of lactones of small to large rings, and a cyclic diester to produce the corresponding polyesters. Also, lipase catalyzes the condensation polymerization of a dialkyl carbonate with diol, and the ring‐opening polymerization of a cyclic carbonate to produce the corresponding polycarbonates. These polyesters and polycarbonates were selectively degraded by lipase to produce repolymerizable oligomers. These chemical recycling systems using an enzyme will establish a novel methodology for sustainable polymer recycling. Finally, current trends in green polymer production using enzymes are discussed.

show abstract

“…So far, enzymatic polymer recycling in the presence of N-435 was conducted for: PLLA [103], PBA [104], PBS [104], PCL [105], PHB [106], poly(trimethylene carbonate) (PTMC) [107], PTCL [108], and in some cases the repolymerization step was also investigated [107].…”

Section: Degradation Of Aliphatic Polyestersmentioning

confidence: 42%

“…Much lower temperature of degradation was applied for poly(R,S)-3-hydroxybutanoate [106] and PCL [109], which were transformed into a reactive cyclic products in toluene, to give oligomers with M n less than 500 g mol −1 . Both polymers were also depolymerized under continuous flow conditions in toluene solution, using enzyme column packed with N-435 [105,110].…”

Section: Degradation Of Aliphatic Polyestersmentioning

confidence: 48%