Chiral differentiation of some cyclic β-amino acids by kinetic and fixed ligand methods

Anna R M Hyyryläinen, Jaana M H Pakarinen, E. Forró, F. Fülöp, Pirjo Vainiotalo

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Differentiation of β-amino acid enantiomers with two chiral centres was investigated by kinetic method with trimeric metal-bound complexes. Four enantiomeric pairs of β-amino acids were studied: cis-(1R,2S)-, cis-(1S,2R)-, trans-(1R,2R)- and trans-(1S,2S)-2-aminocyclopentanecarboxylic acids (cyclopentane β-amino acids), and cis-(1R,2S)-, cis-(1S,2R)-, trans-(1R,2R)-, and trans-(1S,2S)-2-aminocyclohexanecarboxylic acids (cyclohexane β-amino acids). The results showed that the choice of metal ion (Cu2+, Ni2+) and chiral reference compound (α- andβ-amino acids) had an effect on the enantioselectivity. Especially, aromaticity of the reference compound was noted to enhance the enantioselectivity. The fixed-ligand kinetic method, a modification of the kinetic method, was then applied to the same β-amino acids, with dipeptides used as fixed ligands. With this method, dipeptide containing an aromatic side chain enhanced the enantioselectivity.

Original languageEnglish
Pages (from-to)198-204
Number of pages7
JournalJournal of Mass Spectrometry
Volume45
Issue number2
DOIs
Publication statusPublished - Feb 2010

Fingerprint

Cyclic Amino Acids
amino acids
Amino acids
Ligands
Amino Acids
ligands
Kinetics
Enantioselectivity
kinetics
Dipeptides
Cycloleucine
Cyclopentanes
acids
Acids
Enantiomers
Coordination Complexes
enantiomers
Cyclohexane
cyclohexane
Metal ions

Keywords

  • Chiral β-amino acids
  • Enantioselectivity
  • ESI-QIT mass spectrometry
  • The fixed-ligand kinetic method
  • The kinetic method

ASJC Scopus subject areas

  • Spectroscopy

Cite this

Chiral differentiation of some cyclic β-amino acids by kinetic and fixed ligand methods. / Hyyryläinen, Anna R M; Pakarinen, Jaana M H; Forró, E.; Fülöp, F.; Vainiotalo, Pirjo.

In: Journal of Mass Spectrometry, Vol. 45, No. 2, 02.2010, p. 198-204.

Research output: Contribution to journalArticle

Hyyryläinen, Anna R M ; Pakarinen, Jaana M H ; Forró, E. ; Fülöp, F. ; Vainiotalo, Pirjo. / Chiral differentiation of some cyclic β-amino acids by kinetic and fixed ligand methods. In: Journal of Mass Spectrometry. 2010 ; Vol. 45, No. 2. pp. 198-204.
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