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

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Abstract

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][PF6] mediated by the enzyme lipase B from Candida antarctica (Novozyme 435). The highest PLLA yield (63%) was attained at 90 °C with a molecular weight (M n ) of 37.8 × 103 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 °C product synthesis also occurred without biocatalyst, however, PLLA synthesis in [HMIM][PF6] at 65 °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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Acknowledgments

We acknowledge financial support from SEP-CONACyT (project 48641) and scholarships to JRPD and MM. We are also grateful to DGAPA-UNAM for postdoctoral grant (SCh) and project number IN200109 for funding. We thank Novozymes Mexico for biocatalyst samples. We also thank USAI (Facultad de Química-UNAM) for NMR, TGA, DSC and XRD analyses.

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Authors and Affiliations

  1. Departamento de Alimentos y Biotecnología, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510, Mexico, DF, Mexico

    Sébastien Chanfreau, Maria Mena, Jaime R. Porras-Domínguez, Mariana Ramírez-Gilly, Miquel Gimeno, Alberto Tecante & Eduardo Bárzana

  2. Departamento de Ingeniería Química, Facultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, 04510, Mexico, DF, Mexico

    Sébastien Chanfreau & Pedro Roquero

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  1. Sébastien Chanfreau
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  2. Maria Mena
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  3. Jaime R. Porras-Domínguez
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  4. Mariana Ramírez-Gilly
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  5. Miquel Gimeno
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  7. Alberto Tecante
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  8. Eduardo Bárzana
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Correspondence to Miquel Gimeno or Eduardo Bárzana.

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Chanfreau, S., Mena, M., Porras-Domínguez, J.R. et al. Enzymatic synthesis of poly-l-lactide and poly-l-lactide-co-glycolide in an ionic liquid. Bioprocess Biosyst Eng 33, 629–638 (2010). https://doi.org/10.1007/s00449-009-0388-8

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  • DOI: https://doi.org/10.1007/s00449-009-0388-8

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