Multi-residue analysis of chiral and achiral trace organic contaminants in soil by accelerated solvent extraction and enantioselective liquid chromatography tandem–mass spectrometry

Bruce Petrie, Jana Mrazova, Barbara Kasprzyk-Hordern, Kyari Yates

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Reported here is the first analytical methodology for the enantiomeric determination of chiral trace organic contaminants (TOrCs) in soil. Direct enantioselective separations were achieved on a Chirobiotic V2® column operated in polar ionic mode. Initial screening of vancomycin stationary phases found Chirobiotic V2® better suited for multi-residue separation of chiral TOrCs than Chirobiotic V® due to differences in the ligand linkage chemistry. Simultaneous enantioseparation of beta-blockers, beta-agonists, anti-depressants, anti-histamines and stimulants was achieved for the first time. This included the first separation of chlorpheniramine enantiomers with a method suitable for environmental analysis (i.e., coupled to MS). Investigation of mobile phase composition found the concentration of liophilic ions had the greatest influence on enantioseparations and of most importance during method development. The optimized method achieved simultaneous separation of salbutamol, propranolol, atenolol, amphetamine, chlorpheniramine and fluoxetine enantiomers with satisfactory resolution (>1.0). For completeness, such methods also need to support analysis of achiral TOrCs. Therefore three achiral TOrCs (carbamazepine, carbamazepine 10,11 epoxide and triclocarban) were included to demonstrate the methods suitability. Method recoveries for all analytes ranged from 76 to 122% with method quantitation limits (MQLs) <1 ng g−1. Application of the method to soil microcosm studies revealed stereoselective degradation of chiral TOrCs for the first time. For example, S(+)-amphetamine degraded at a faster rate than its corresponding enantiomer leading to an enrichment of R(−)-amphetamine. Therefore to better understand the risk posed from TOrCs on the terrestrial environment, chiral species need profiled at the enantiomeric level. This can now be addressed using the proposed methodology whilst simultaneously profiling achiral TOrCs.

Original languageEnglish
Pages (from-to)62-71
Number of pages10
JournalJournal of Chromatography A
Volume1572
Early online date19 Aug 2018
DOIs
Publication statusPublished - 19 Oct 2018

Keywords

  • Chiral
  • LC–MS/MS
  • Micropollutant
  • Pharmaceutical
  • Sludge
  • Soil

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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