Determination of ᴅ-phenylglycine in the presence of its ʟ-enantiomer using a turn-on fluorescent nano-chemosensor

Talanta. 2017 Jan 1:162:547-551. doi: 10.1016/j.talanta.2016.10.054. Epub 2016 Oct 13.

Abstract

This paper reports on application of ʟ-tryptophan modified magnetite nanospheres (TryMNSs) as a novel fluorescent chiral selector for selective and sensitive determination of ᴅ-phenylglycine (ᴅ-Phy) in the presence of its enantiomer (i.e. ʟ-phenylglycine, ʟ-Phy). The results showed that the nanospheres could be used as a "turn-on" fluorescence nanosensor based on enhancement of its fluorescence peak intensity in the presence of ᴅ-Phy. Unlike its enantiomer, ʟ-Phy did not affect the nanosensor fluorescence behaviour suggesting that using the synthesized nanospheres selective determination of ᴅ-Phy in the presence of ʟ-Phy was achievable. The enhancing effect can be attributed to the initial formation of hydrogen-bonded complex followed by π-π interaction between the aromatic tryptophan moieties and ᴅ-Phy. After various affecting factors optimizing, the results showed that using the enhancing effect, selective and sensitive determination of ᴅ-Phy in the presence of ʟ-Phy in the concentration range of 0.5-200.0mgL-1 with a detection limit as low as 190ngmL-1 was achievable.

Keywords: Chiral chemosensor; Determination; Enantioselective recognition; Fluorescence; Magnetite nanospheres; ᴅ-phenylglycine.

MeSH terms

  • Ferrosoferric Oxide / chemistry
  • Fluorescence*
  • Fluorescent Dyes / chemistry*
  • Glycine / analogs & derivatives*
  • Glycine / analysis
  • Glycine / chemistry
  • Hydrogen-Ion Concentration
  • Microscopy, Electron, Transmission
  • Nanospheres / chemistry*
  • Nanospheres / ultrastructure
  • Reproducibility of Results
  • Sonication
  • Spectroscopy, Fourier Transform Infrared / methods*
  • Stereoisomerism

Substances

  • Fluorescent Dyes
  • N-phenylglycine
  • Glycine
  • Ferrosoferric Oxide