Synthesis and structural characterization of N-methyl-DL-glutamic acid

Andrew B. Hughes, Maureen F. Mackay, Luigi Aurelio

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The solid-state conformation of racemic N-methylglutamic acid has been defined by single-crystal X-ray crystallography. Orthorhombic crystals belong to the space group P bca with a 15.219(2), b 10.583(1), c 9.595(1) Å and Z 8. The structure was refined to a final R value of 0.049 for the 1285 measured data. In the crystal the molecules adopt a zwitterionic form with protonation having occurred at the amino nitrogen atom. The α-carboxyl is unprotonated with the δ-carboxy group retaining a proton. The i.r. spectrum shows absorptions which also are indicative of the amino acid being in the zwitterionic form. Intermolecular H-bonds involving the carboxylate proton and the two protons on the N-atom link the molecules into a three-dimensional network in the crystal.

Original languageEnglish
Pages (from-to)237-240
Number of pages4
JournalAustralian Journal of Chemistry
Issue number3
Publication statusPublished - 1 Dec 2000
Externally publishedYes


  • Glutamic acid
  • Peptide
  • X-Ray crystallography
  • Zwitterion

Cite this

Hughes, A. B., Mackay, M. F., & Aurelio, L. (2000). Synthesis and structural characterization of N-methyl-DL-glutamic acid. Australian Journal of Chemistry, 53(3), 237-240.