Characterization and quantification of racemic and meso-ethylenediamine-N,N'-bis(2-hydroxy-5-sulfophenylacetic) acid/iron (III) by ion-pair ultra-high performance liquid chromatography coupled with diode array detector and electrospray tandem mass spectrometry

J Chromatogr A. 2013 Mar 22:1282:142-52. doi: 10.1016/j.chroma.2013.01.083. Epub 2013 Jan 26.

Abstract

EDDHSA/Fe is a promising substitute of EDDHA/Fe to fight iron chlorosis. o,o-EDDHSA structure contains two chiral carbons giving the racemic and meso couples of stereoisomers. Ion-pair HPLC and UHPLC-UV/Vis-ESI-MS/MS methods were developed for the determination of racemic and meso-o,o-EDDHSA/Fe in commercial samples of chelates. The lack of a commercial EDDHSA standard was overcome by sulfonation of a commercial available o,o-EDDHA standard and subsequent quantification by (1)H-NMR. Assignment of configurations was carried out starting from racemic and meso-o,o-EDDHA/Fe by direct sulfonation to give the corresponding o,o-EDDHSA/Fe isomers. The performances of these methods were assessed in terms of intra and inter-day precision, linearity and selectivity. The high selectivity and lower detection limit (nanomolar) of the UHPLC-ESI-MS/MS method could allow to deepen the knowledge relative to meso and rac-o,o-EDDHSA/Fe interactions with plants, its fate in different soil conditions, its mobility and other environmental aspects.

MeSH terms

  • Acetonitriles / chemistry
  • Acids, Acyclic / chemistry
  • Chromatography, High Pressure Liquid / methods*
  • Hydrochloric Acid / chemistry
  • Ions / analysis
  • Ions / chemistry
  • Iron / analysis*
  • Iron / chemistry*
  • Limit of Detection
  • Phenylacetates / analysis*
  • Phenylacetates / chemistry*
  • Reproducibility of Results
  • Sensitivity and Specificity
  • Spectrometry, Mass, Electrospray Ionization
  • Stereoisomerism
  • Tandem Mass Spectrometry / methods*

Substances

  • Acetonitriles
  • Acids, Acyclic
  • Ions
  • N,N'-ethylenediamine-di-(2-hidroxy-5-sulfophenylacetic) acid
  • Phenylacetates
  • Iron
  • Hydrochloric Acid
  • acetonitrile