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Synthesis of lactate (LA)-based poly(ester-urethane) using hydroxyl-terminated LA-based oligomers from a microbial secretion system

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Abstract

D-Lactate (LA)-based oligomers (D-LAOs), consisting of D-LA and D-3-hydroxybutyrate (D-3HB), are biobased compounds which are produced and spontaneously secreted by recombinant Escherichia coli. By supplementing the bacterial cultivation with diethylene glycol (DEG), the oligomers featuring hydroxyl groups at both ends of their structures, the D-LAOs-DEG, can be efficiently biosynthesized. In the present work, we attempted to verify the feasibility of D-LAOs-DEG as building blocks to be assembled into LA-based poly(ester-urethane) via polyaddition reaction with diisocyanate. The polymeric products were demonstrated by SEC and the urethane bound formation in the polymer was determined by FT-IR analysis, indicating that the polymerization was successfully performed. These results suggested that the one-step biosynthesized D-LAOs-DEG are potential substrates for the synthesis of LA-based poly(ester-urethane) and can be further applied to the synthesis of other LA copolymers.

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Acknowledgements

ESI-TOF-MS was measured using the Open Facility of the Center for Advanced Research of Energy Conversion Material, Hokkaido University. This study was partially supported by CREST, JST (JPMJCR12B4 to S.T. and K.M.).

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Author notes

  1. Seiichi Taguchi

    Present address: Department of Chemistry for Life Sciences and Agriculture, Faculty of Life Sciences, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya-ku, Tokyo, 156-8502, Japan

Authors and Affiliations

  1. Graduate School of Chemical Sciences and Engineering, Hokkaido University, N13-W8, Kita-ku, Sapporo, 060-8628, Japan

    Camila Utsunomia & Tatsuya Saito

  2. Division of Applied Chemistry, Faculty of Engineering, Hokkaido University, N13-W18, Kita-ku, Sapporo, 060-8628, Japan

    Ken’ichiro Matsumoto, Chiaki Hori, Takuya Isono, Toshifumi Satoh & Seiichi Taguchi

  3. CREST, JST, 4-1-8 Honcho, Kawaguchi, Saitama, 332-0012, Japan

    Ken’ichiro Matsumoto, Chiaki Hori & Seiichi Taguchi

Authors
  1. Camila Utsunomia
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  2. Tatsuya Saito
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  3. Ken’ichiro Matsumoto
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  4. Chiaki Hori
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  5. Takuya Isono
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  6. Toshifumi Satoh
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  7. Seiichi Taguchi
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Corresponding author

Correspondence to Seiichi Taguchi.

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Utsunomia, C., Saito, T., Matsumoto, K. et al. Synthesis of lactate (LA)-based poly(ester-urethane) using hydroxyl-terminated LA-based oligomers from a microbial secretion system. J Polym Res 24, 167 (2017). https://doi.org/10.1007/s10965-017-1325-1

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  • DOI: https://doi.org/10.1007/s10965-017-1325-1

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