Advertisement

Journal of Polymer Research

, 24:167 | Cite as

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

  • Camila Utsunomia
  • Tatsuya Saito
  • Ken’ichiro Matsumoto
  • Chiaki Hori
  • Takuya Isono
  • Toshifumi Satoh
  • Seiichi TaguchiEmail author
SHORT COMMUNICATION
Part of the following topical collections:
  1. Topical Collection on Bio-Based Polymers

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.

Keywords

Polyhydroxyalkanoate Polylactic acid Oligoester Biobased plastic Polyurethane Microbial factory 

Notes

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.).

References

  1. 1.
    Utsunomia C, Matsumoto K, Taguchi S (2017) Microbial secretion of D-lactate-based oligomers. ACS Sustain Chem Eng 5:2360–2367CrossRefGoogle Scholar
  2. 2.
    Utsunomia C, Chiaki H, Matsumoto K, Taguchi S (2017) Investigation of the Escherichia coli membrane transporters involved in the secretion of D-lactate-based oligomers by loss-of-function screening. J Biosci Bioeng.  https://doi.org/10.1016/j.jbiosc.2017.06.018
  3. 3.
    Taguchi S, Yamada M, Matsumoto K, Tajima K, Satoh Y, Munekata M, Ohno K, Kohda K, Shimamura T, Kambe H (2008) A microbial factory for lactate-based polyesters using a lactate-polymerizing enzyme. Proc Natl Acad Sci U S A 105:17323–17327CrossRefGoogle Scholar
  4. 4.
    Yamada M, Matsumoto K, Shimizu K, Uramoto S, Nakai T, Shozui F, Taguchi S (2010) Adjustable mutations in lactate (LA)-polymerizing enzyme for the microbial production of LA-based polyesters with tailor-made monomer composition. Biomacromolecules 11:815–819CrossRefGoogle Scholar
  5. 5.
    Utsunomia C, Matsumoto K, Date S, Hori C, Taguchi S (2017) Microbial secretion of lactate-enriched oligomers for efficient conversion into lactide: a biological shortcut to polylactide. J Biosci Bioeng 124:204–208CrossRefGoogle Scholar
  6. 6.
    Nampoothiri KM, Nair NR, John RP (2010) An overview of the recent developments in polylactide (PLA) research. Bioresour Technol 101:8493–8501CrossRefGoogle Scholar
  7. 7.
    Masutani K, Kimura Y (2015) In: Jiménez A, Peltzer M, Ruseckaite R (ed) Poly(lactic acid) science and technology: processing, properties, additives, and applications, 1st edn. The Royal Society of Chemistry, CambridgeGoogle Scholar
  8. 8.
    Inkinen S, Hakkarainen M, Albertsson A-C, Södergård A (2011) From lactic acid to poly(lactic acid) (PLA): characterization and analysis of PLA and its precursors. Biomacromolecules 12:523–532CrossRefGoogle Scholar
  9. 9.
    Tuominen J, Kylmä J, Seppälä J (2002) Chain extending of lactic acid oligomers. 2. Increase of molecular weight with 1, 6-hexamethylene diisocyanate and 2, 2′-bis (2-oxazoline). Polymer 43:3–10CrossRefGoogle Scholar
  10. 10.
    Ren J, Wang QF, Gu SY, Zhang NW, Ren TB (2006) Chain-linked lactic acid polymers by benzene diisocyanate. J Appl Polym Sci 99:1045–1049CrossRefGoogle Scholar
  11. 11.
    Zia KM, Bhatti HN, Bhatti IA (2007) Methods for polyurethane and polyurethane composites, recycling and recovery: a review. React Funct Polym 67:675–692CrossRefGoogle Scholar
  12. 12.
    Hiltunen K, Seppälä JV, Härkönen M (1997) Lactic acid based poly(ester-urethanes): use of hydroxyl terminated prepolymer in urethane synthesis. J Appl Polym Sci 63:1091–1100CrossRefGoogle Scholar
  13. 13.
    Stolt M, Hiltunen K, Södergård A (2001) Use of iron monocarboxylates in the two-step preparation of poly(ester-urethane)s. Biomacromolecules 2:1243–1248CrossRefGoogle Scholar
  14. 14.
    Gu S, Yang M, Yu T, Ren T, Ren J (2008) Synthesis and characterization of biodegradable lactic acid-based polymers by chain extension. Polym Int 57:982–986CrossRefGoogle Scholar
  15. 15.
    Baba T, Ara T, Hasegawa M, Takai Y, Okumura Y, Baba M, Datsenko KA, Tomita M, Wanner BL, Mori H (2006) Construction of Escherichia coli K-12 in-frame, single-gene knockout mutants: the Keio collection. Mol Syst Biol 2:2006.0008CrossRefGoogle Scholar
  16. 16.
    Saito T, Aizawa Y, Tajima K, Isono T, Satoh T (2015) Organophosphate-catalyzed bulk ring-opening polymerization as an environmentally benign route leading to block copolyesters, end-functionalized polyesters, and polyester-based polyurethane. Polym Chem 6:4374–4384CrossRefGoogle Scholar
  17. 17.
    Yamada M, Matsumoto K, Nakai T, Taguchi S (2009) Microbial production of lactate-enriched poly[(R)-lactate-co-(R)-3-hydroxybutyrate] with novel thermal properties. Biomacromolecules 10:677–681CrossRefGoogle Scholar
  18. 18.
    Tuominen J, Seppälä JV (2000) Synthesis and characterization of lactic acid based poly(ester-amide). Macromolecules 33:3530–3535CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2017

Authors and Affiliations

  • Camila Utsunomia
    • 1
  • Tatsuya Saito
    • 1
  • Ken’ichiro Matsumoto
    • 2
    • 3
  • Chiaki Hori
    • 2
    • 3
  • Takuya Isono
    • 2
  • Toshifumi Satoh
    • 2
  • Seiichi Taguchi
    • 2
    • 3
    • 4
    Email author
  1. 1.Graduate School of Chemical Sciences and EngineeringHokkaido UniversitySapporoJapan
  2. 2.Division of Applied Chemistry, Faculty of EngineeringHokkaido UniversitySapporoJapan
  3. 3.CREST, JSTSaitamaJapan
  4. 4.Department of Chemistry for Life Sciences and Agriculture, Faculty of Life SciencesTokyo University of AgricultureTokyoJapan

Personalised recommendations