Synthesis of Dianionic and Trianionic Chiral, Chelating Ligands Based on Amino Acids

Madeleine Schultz; Jakov Kulis; Julie Murison; Genevieve W. Andrews

doi:10.1071/CH07430

RESEARCH ARTICLE

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Synthesis of Dianionic and Trianionic Chiral, Chelating Ligands Based on Amino Acids

Madeleine Schultz ^A ^C , Jakov Kulis ^B , Julie Murison ^B and Genevieve W. Andrews ^A

+ Author Affiliations

- Author Affiliations

^A School of Physical and Chemical Sciences, Queensland University of Technology, Brisbane, Qld 4001, Australia.

^B School of Molecular and Microbial Sciences, University of Queensland, St Lucia, Qld 4072, Australia.

^C Corresponding author. Email: madeleine.schultz@qut.edu.au

Australian Journal of Chemistry 61(4) 297-302 https://doi.org/10.1071/CH07430
Submitted: 13 December 2007 Accepted: 17 March 2008 Published: 24 April 2008

Abstract

The synthesis of two new families of amino acid-containing chiral ligands, based on methyliminodiacetic acid and nitrilotriacetic acid cores, has been accomplished using a simple protection, solution-phase amide coupling, and deprotection strategy. The amino acids glycine, leucine, aspartic acid, and phenylalanine were used to demonstrate the versatility of the synthetic route, and that no epimerization occurs. The tridentate ligands bear C₃ symmetry, whereas the bidentate ligands have C₁ symmetry.

Acknowledgements

J.K. acknowledges UniChe for a summer scholarship. We thank Dr Joanne Blanchfield for helpful discussions.

References

Synthesis of Dianionic and Trianionic Chiral, Chelating Ligands Based on Amino Acids

Abstract

Acknowledgements

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