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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Synthesis and Structural Characterization of N-Methyl-DL-glutamic Acid

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

Australian Journal of Chemistry 53(3) 237 - 240
Published: 2000

Abstract

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 Pbca 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 a-carboxyl is unprotonated with the d-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.

Keywords: X-Ray crystallography; zwitterion; glutamic acid; peptide.

https://doi.org/10.1071/CH99182

© CSIRO 2000

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