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Monatshefte für Chemie - Chemical Monthly

, Volume 150, Issue 2, pp 247–253 | Cite as

An optimized method for an (2R,3S)-isocitric acid building block

  • Kristin Bullin
  • Lothar Hennig
  • Renate Herold
  • Harald Krautscheid
  • Karin Richter
  • Dieter SickerEmail author
Original Paper
  • 69 Downloads

Abstract

An optimized method for (2R,3S)-isocitric acid lactone-2,3-dicarboxylic acid dimethyl ester as an (2R,3S)-isocitric acid building block based on a fermentation solution containing both (2R,3S)-isocitric acid (ICIT) and citric acid is described. The number of operations needed until now has been reduced; some steps have been modified, making altogether the method distinctly faster. During the course of this investigation, crystal structures have been determined of (2R,3S)-isocitric acid lactone-2,3-dicarboxylic acid dimethyl ester, (2R,3S)-isocitric acid lactone-2,3-dicarboxylic acid, and (2R,3S)-isocitric acid lactone-2,3-dicarboxylic acid anhydride. For the first time, full NMR data are given for ICIT trimethyl ester and ICIT lactone-2,3-dicarboxylic acid dimethyl ester. The multigram amounts of the three ICIT lactone compounds open the way for the synthetic use of ICIT generated in a biotechnological process.

Graphical abstract

Keywords

Bioorganic chemistry Separation Optimization Carboxylic acids Isomers Crystal structure 

Notes

Acknowledgements

We are grateful to Katrin Hoffmann and Tamara Meinel for their unimpeachable support with NMR measurements throughout many years. We thank Prof. Dr. Joachim Sieler for his continuous support of our investigations.

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Institute of Organic ChemistryUniversität LeipzigLeipzigGermany
  2. 2.Institute of Inorganic ChemistryUniversität LeipzigLeipzigGermany

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