Manipulating selectivity of covalently-bonded hyperbranched anion exchangers toward organic acids. Part II: Effect of mono- and dicarboxylic amino acids in the internal part of the functional layer

J Chromatogr A. 2019 Jul 5:1596:117-123. doi: 10.1016/j.chroma.2019.03.006. Epub 2019 Mar 7.

Abstract

Four covalently-bonded hyperbranched anion exchangers based on poly(styrene-divinylbenzene) (PS-DVB) substrate with different structure of the functional layer were prepared using mono- and dianionic amino acids such as glycine, β-alanine, aspartic acid, and glutamic acid in the internal part of the functional layer. Selectivity of all anion exchangers toward weakly retained organic acids was investigated at different temperatures in order to evaluate the effect of the number of carboxylic groups in the functional layer and its hydrophilicity on the separation. It was found that dianionic amino acids used in the first modification cycle of hyperbranching provide the best resolution for mono- and divalent organic acids, which makes the number of carboxylic groups in the structure of amino acid a key factor in the separation of such analytes with covalently-bonded hyperbranched anion exchangers, while the role of amino acid hydrophilicity is not that significant. Stationary phases prepared using aspartic and glutamic acids provided baseline resolution for quinic, glycolic, acetic, lactic, formic, and galacturonic acids, which are not resolved to baseline with modern commercially available anion exchangers; the increase of temperature was found to be favorable for improving the resolution even further.

Keywords: Amino acids; Covalently-bonded anion exchanger; Hyperbranched functional layer; Ion chromatography; Negatively charged functionalities; Organic acids.

MeSH terms

  • Amino Acids / chemistry*
  • Amino Acids / isolation & purification
  • Amino Acids, Dicarboxylic / chemistry*
  • Anion Exchange Resins / chemistry*
  • Chromatography, Ion Exchange
  • Hydrophobic and Hydrophilic Interactions
  • Organic Chemicals / chemistry
  • Polystyrenes / chemistry
  • Temperature

Substances

  • Amino Acids
  • Amino Acids, Dicarboxylic
  • Anion Exchange Resins
  • Organic Chemicals
  • Polystyrenes
  • Amberlite XAD-2 resin