Unique Complexation Behavior of Alkali Metal Ions and 2-Pyrone-4,6-Dicarboxylic Acid (PDC) Obtained from a Metabolic Intermediate of Lignin

  • Masami Bito
  • Yuichiro Otsuka
  • Masaya Nakamura
  • Eiji Masai
  • Yoshihiro Katayama
  • Kiyotaka Shigehara
  • Kazuhiro Shikinaka
Original Paper


The complexation behavior between 2-pyrone-4,6-dicarboxylic acid (PDC) and alkali metal ions was systematically estimated. The PDC complexes of alkali metal ions exhibit unique crystal structures due to the diverse coordination numbers of the metal ion. The crystal structure of the complex between PDC and cesium (Cs) ion suggests that the metal ion binary crosslinking and much coordination numbers of the Cs induce the preferential complex formation via sedimentation of the PDC–Cs complex. The minor electronegativity difference between the Cs and other alkali metals might be the determining factor in the structure of the complex the ion forms with PDC.


Woody biomass Lignin 2-Pyrone-4,6-dicarboxylic acid Alkali metal ion Sedimentation reagents 



The authors gratefully acknowledge the financial support of JSPS KAKENHI (Grant Number 24380180 and 24780172) and Sugiyama Chemical & Industrial Lab. The measurements of single-crystal X-ray diffraction were conducted in Research Hub for Advanced Nano Characterization, The University of Tokyo, supported by the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan. We thank Prof. Dr. Yoshiki Ozawa (University of Hyogo) and Professor Emeritus Kazuyuki Horie (The University of Tokyo) for their kind assistance on synchrotron orbital X-ray scattering experiments.

Supplementary material

12649_2017_147_MOESM1_ESM.docx (23 kb)
Supplementary material 1 (DOCX 23 KB)


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Copyright information

© Springer Science+Business Media B.V., part of Springer Nature 2017

Authors and Affiliations

  • Masami Bito
    • 1
  • Yuichiro Otsuka
    • 2
  • Masaya Nakamura
    • 2
  • Eiji Masai
    • 3
  • Yoshihiro Katayama
    • 4
  • Kiyotaka Shigehara
    • 5
  • Kazuhiro Shikinaka
    • 6
  1. 1.J-CHEMICAL, INC.TokyoJapan
  2. 2.Forestry and Forest Products Research InstituteTsukubaJapan
  3. 3.Department of BioengineeringNagaoka University of TechnologyNagaokaJapan
  4. 4.College of Bioresource ScienceNihon UniversityFujisawaJapan
  5. 5.Graduate School of EngineeringTokyo University of Agriculture and TechnologyTokyoJapan
  6. 6.Research Institute for Chemical Process TechnologyNational Institute of Advanced Industrial ScienceSendaiJapan

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