Chiral analysis of biogenic DL-amino acids derivatized by urethane - Protected α-amino acid N-carboxyanhydride using capillary zone electrophoresis and micellar electrokinetic chromatography

Martin Pumera, Martin Flegel, Luděk Lepša, Ivan Jelínek

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A new analytical method for enantioselective separation of DL-amino acids derivatized by N-fluorenylmethoxycarbonyl-L-alanyl N-carboxyanhydride (FMOC-L-Ala-NCA) using capillary electrophoresis was developed. Separation parameters, such as composition and pH of the background electrolyte, and concentration of γ-cyclodextrin (in capillary zone electrophoresis) and sodium dodecyl sulfate (in micellar electrokinetic chromatography) were optimized. The separation method was validated and it suits well for purity analysis. Detection limit of the method was 0.2% of the minor enantiomer in the major one. The level of racemization in coupling during solid-phase pepticle synthesis was studied using capillary electrophoresis with γ-cyclodextrin as a chiral selector. The anchorage of the first (C-terminal) amino acid derivative to the solid supports bearing the hydroxylic groups is the key step of the synthesis affecting the extent of its racemization. FMOC-L-phenylalanine was chosen as the suitable model amino acid derivative making it possible to study the degree of racemization of N-fluorenylmethoxycarbonyl-L-alanine-L-phenylalanine synthesized on different polymer resins, using the different condensation agent.

Original languageEnglish
Pages (from-to)2449-2456
Number of pages8
JournalElectrophoresis
Volume23
Issue number15
DOIs
Publication statusPublished - 2002 Aug 1

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Urethane
Capillary Electrophoresis
Chromatography
Electrophoresis
Capillary electrophoresis
Cyclodextrins
Phenylalanine
Amino Acids
Bearings (structural)
Derivatives
Solid-Phase Synthesis Techniques
Enantiomers
Sodium Dodecyl Sulfate
Alanine
Electrolytes
Limit of Detection
Condensation
Polymers
Resins
Chemical analysis

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry

Cite this

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abstract = "A new analytical method for enantioselective separation of DL-amino acids derivatized by N-fluorenylmethoxycarbonyl-L-alanyl N-carboxyanhydride (FMOC-L-Ala-NCA) using capillary electrophoresis was developed. Separation parameters, such as composition and pH of the background electrolyte, and concentration of γ-cyclodextrin (in capillary zone electrophoresis) and sodium dodecyl sulfate (in micellar electrokinetic chromatography) were optimized. The separation method was validated and it suits well for purity analysis. Detection limit of the method was 0.2{\%} of the minor enantiomer in the major one. The level of racemization in coupling during solid-phase pepticle synthesis was studied using capillary electrophoresis with γ-cyclodextrin as a chiral selector. The anchorage of the first (C-terminal) amino acid derivative to the solid supports bearing the hydroxylic groups is the key step of the synthesis affecting the extent of its racemization. FMOC-L-phenylalanine was chosen as the suitable model amino acid derivative making it possible to study the degree of racemization of N-fluorenylmethoxycarbonyl-L-alanine-L-phenylalanine synthesized on different polymer resins, using the different condensation agent.",
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Chiral analysis of biogenic DL-amino acids derivatized by urethane - Protected α-amino acid N-carboxyanhydride using capillary zone electrophoresis and micellar electrokinetic chromatography. / Pumera, Martin; Flegel, Martin; Lepša, Luděk; Jelínek, Ivan.

In: Electrophoresis, Vol. 23, No. 15, 01.08.2002, p. 2449-2456.

Research output: Contribution to journalArticle

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