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

  1. Yosuke Takahashi,
  2. Sachiko Okajima,
  3. Kazunobu Toshima,
  4. Shuichi Matsumura*

Article first published online: 23 MAR 2004

DOI: 10.1002/mabi.200300094

Issue

Macromolecular Bioscience

Macromolecular Bioscience

Special Issue: Highlights from the First IUPAC International Conference on Bio-based Polymers (ICBP 2003) in Saitama, Japan

Volume 4, Issue 3, pages 346–353, March 15, 2004

Additional Information

How to Cite

Takahashi, Y., Okajima, S., Toshima, K. and Matsumura, S. (2004), Lipase-Catalyzed Transformation of Poly(lactic acid) into Cyclic Oligomers. Macromol. Biosci., 4: 346–353. doi: 10.1002/mabi.200300094

Author Information

  1. Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan

*Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. Fax: (+81) 45-566-1582

Publication History

  1. Issue published online: 23 MAR 2004
  2. Article first published online: 23 MAR 2004
  3. Manuscript Accepted: 9 JAN 2004
  4. Manuscript Revised: 24 DEC 2003
  5. Manuscript Received: 8 NOV 2003

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Keywords:

  • degradation;
  • enzymes;
  • oligomers;
  • poly(lactic acid);
  • recycling

Abstract

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Summary: 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 equation image of 84 000) was quantitatively transformed into cyclic oligomers by lipase RM (Lipozyme RM IM) in chloroform/hexane at 60 °C. PLLA (with a equation image of 120 000) was transformed into cyclic oligomer by lipase CA (Novozym 435) at a higher temperature of 100 °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.

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