One-pot Enzymatic Synthesis of Poly(L,L-lactide) by Immobilized Lipase Catalyst

Fujioka, Masayori; Hosoda, Naoki; Nishiyama, Satoko; Noguchi, Hirohisa; Shoji, Atsumu; Kumar, D. Sakthi; Katsuraya, Kaname; Ishii, Shigeru; Yoshida, Yasuhiko

doi:10.2115/fiber.62.63

Cited by 19 publications

(14 citation statements)

References 8 publications

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“…Its 1H-NMR analyses showed that 15% of LLA was consumed after one day and it was completely depleted after 7 days. On the basis of our experimental results, which are similar to earlier reported works [7,8], it can be concluded that, ROP of LLA proceeds without biocatalyst both in IL media and in bulk. In addition, 1H-NMR, 13C NMR (Fig.…”

Section: Resultssupporting

confidence: 92%

“…3) were obtained after 3 days of reaction without biocatalyst (Table 1). This same result has been reported in the synthesis in bulk using this biocatalyst [8] and other enzymatic preparations [7,11].…”

Section: Resultssupporting

confidence: 87%

“…Aliquots of the reaction media were taken to monitor the conversions of LLA. To this end, the integration intensities of the d = 5.0 ppm signal in 1H-NMR assigned to the methine hydrogen of the monomer, were compared with the proton signal at d = 5.2 ppm assigned to the same atom in the linear forms as reported elsewhere [7,8]. Variation in LLA conversions versus reaction time for selected experiments is shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Matsumura et al [7] were the first to report the bulk polymerization of LLA (mp: 92°C) with low PLLA yields (16%) using lipase from Burkholderia (formerly Pseudomonas) cepacia (lipase PS). Recently, some authors have claimed that it is possible to synthesize PLLA in bulk [8], as well as other poly(hydroxyalkanoates) in ionic liquids (ILs), using the readily available immobilized lipase B from Candida antarctica (CALB) in its commercial form Novozyme 435 [9,10]. It has been reported that by increasing reaction temperatures, substantial increases in yields and polymer molecular weights can be obtained [10].…”

Section: Introductionmentioning

confidence: 99%

“…It has been reported that by increasing reaction temperatures, substantial increases in yields and polymer molecular weights can be obtained [10]. However, in bulk experiments, PLLA is also obtained even in the absence of biocatalyst [8]. Previous reports on the synthesis of PLLGA are restricted to the work of Huijser et al who used lipase PS in bulk at relatively high temperatures (100-130°C), and paid particular attention to elucidating PLGA structures and topology from MALDIToF-MS data, using an ''in-house developed software'' [11].…”

Section: Introductionmentioning

confidence: 99%

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Enzymatic synthesis of poly-l-lactide and poly-l-lactide-co-glycolide in an ionic liquid

Chanfreau

Mena

Porras-Domínguez

et al. 2009

Bioprocess Biosyst Eng

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The syntheses of poly-L-lactide (PLLA) and poly-L-lactide-co-glycolide (PLLGA) is reported in the ionic liquid 1-hexyl-3-methylimidazolium hexafluorophosphate [HMIM][PF(6)] mediated by the enzyme lipase B from Candida antarctica (Novozyme 435). The highest PLLA yield (63%) was attained at 90 degrees C with a molecular weight (M(n)) of 37.8 x 10(3) g/mol determined by size exclusion chromatography. This procedure produced relatively high crystalline polymers (up to 85% PLLA) as determined by DSC. In experiments at 90 degrees C product synthesis also occurred without biocatalyst, however, PLLA synthesis in [HMIM][PF(6)] at 65 degrees C followed only the enzymatic mechanism as ring opening was not observed without the enzyme. In addition, the enzymatic synthesis of PLLGA is first reported here using Novozyme 435 biocatalyst with up to 19% of lactyl units in the resulting copolymer as determined by NMR. Materials were also characterized by TGA, MALDI-TOF-MS, X-ray diffraction, polarimetry and rheology.

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Section: Resultssupporting

confidence: 92%

Section: Resultssupporting

confidence: 87%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Enzymatic synthesis of poly-l-lactide and poly-l-lactide-co-glycolide in an ionic liquid

Chanfreau

Mena

Porras-Domínguez

et al. 2009

Bioprocess Biosyst Eng

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Biocatalyzed approach for the surface functionalization of poly(L‐lactic acid) films using hydrolytic enzymes

Pellis

Acero

Weber

et al. 2015

Biotechnology Journal

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Poly(lactic acid) as a biodegradable thermoplastic polyester has received increasing attention. This renewable polyester has found applications in a wide range of products such as food packaging, textiles and biomedical devices. Its major drawbacks are poor toughness, slow degradation rate and lack of reactive side-chain groups. An enzymatic process for the grafting of carboxylic acids onto the surface of poly(L-lactic acid) (PLLA) films was developed using Candida antarctica lipase B as a catalyst. Enzymatic hydrolysis of the PLLA film using Humicola insolens cutinase in order to increase the number of hydroxyl and carboxylic groups on the outer polymer chains for grafting was also assessed and showed a change of water contact angle from 74.6 to 33.1° while the roughness and waviness were an order of magnitude higher in comparison to the blank. Surface functionalization was demonstrated using two different techniques, (14) C-radiochemical analysis and X-ray photoelectron spectroscopy (XPS) using (14) C-butyric acid sodium salt and 4,4,4-trifluorobutyric acid as model molecules, respectively. XPS analysis showed that 4,4,4-trifluorobutyric acid was enzymatically coupled based on an increase of the fluor content from 0.19 to 0.40%. The presented (14) C-radiochemical analyses are consistent with the XPS data indicating the potential of enzymatic functionalization in different reaction conditions.

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Enzymatic Ring‐Opening Polymerization of Lactones: Traditional Approaches and Alternative Strategies

et al. 2019

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Biodegradable polymers such as polylactides and other polylactones and their synthesis gain progressively importance. Enzymatic ring‐opening polymerization (eROP) is the next step sustainable synthesis of polyesters, also suitable for biomedical applications due to high selectivity and lack of toxic agents. The possibility for applying diverse reaction media ranging from traditional bulk and organic media to greener alternatives such as aqueous media, ionic liquids, and supercritical fluids may allow designing alternative non‐conventional processes with less environmental footprint. Target success criteria such as high molecular weight and uniformity of polymers, and conversion of monomers have to be carefully evaluated in these diverse media. Herein we discuss the influence of different reaction media and conditions such as water content, temperature and time on the polymer sizes achieved in eROPs and various approaches to improve the molecular weight and uniformity of polymers.

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One-pot Enzymatic Synthesis of Poly(L,L-lactide) by Immobilized Lipase Catalyst

Cited by 19 publications

References 8 publications

Enzymatic synthesis of poly-l-lactide and poly-l-lactide-co-glycolide in an ionic liquid

Enzymatic synthesis of poly-l-lactide and poly-l-lactide-co-glycolide in an ionic liquid

Biocatalyzed approach for the surface functionalization of poly(L‐lactic acid) films using hydrolytic enzymes

Enzymatic Ring‐Opening Polymerization of Lactones: Traditional Approaches and Alternative Strategies

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