Non-linear effects in the enantiomeric separation of mandelic acid using the mixtures of amphoteric resolving agents

Zsolt Szeleczky, Péter Bagi, Balázs Fodi, Sándor Semsey, Emese Pálovics, F. Faigl, E. Fogassy

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Abstract In this study, (S)-phenylalanine, aspartame and (S)-pregabalin, which contain α-, β- and γ-amino acidic moieties were successfully applied as resolving agents for the enantiomeric separation of mandelic acid via the formation of diastereomeric salts. The resolution of mandelic acid was also attempted with mixtures of the corresponding resolving agents and a more efficient enantiomeric separation of the mandelic acid was observed compared with the given sole resolving agents in a few instances. The best results were obtained with a mixture of (S)-phenylalanine and (S)-alanine; the latter resolving agent was insufficient when it was applied alone. The resolution efficiency of mandelic acid could also be improved by applying structurally related amphoteric achiral additives along with the corresponding resolving agents.

Original languageEnglish
Article number59314
Pages (from-to)721-731
Number of pages11
JournalTetrahedron Asymmetry
Volume26
Issue number14
DOIs
Publication statusPublished - Jul 6 2015

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acids
Acids
phenylalanine
Phenylalanine
Aspartame
alanine
Alanine
Salts
mandelic acid
salts

ASJC Scopus subject areas

  • Organic Chemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Catalysis

Cite this

Non-linear effects in the enantiomeric separation of mandelic acid using the mixtures of amphoteric resolving agents. / Szeleczky, Zsolt; Bagi, Péter; Fodi, Balázs; Semsey, Sándor; Pálovics, Emese; Faigl, F.; Fogassy, E.

In: Tetrahedron Asymmetry, Vol. 26, No. 14, 59314, 06.07.2015, p. 721-731.

Research output: Contribution to journalArticle

Szeleczky, Zsolt ; Bagi, Péter ; Fodi, Balázs ; Semsey, Sándor ; Pálovics, Emese ; Faigl, F. ; Fogassy, E. / Non-linear effects in the enantiomeric separation of mandelic acid using the mixtures of amphoteric resolving agents. In: Tetrahedron Asymmetry. 2015 ; Vol. 26, No. 14. pp. 721-731.
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