Chiral lumazines: Preparation, properties, enantiomeric separation

Roger Klein, Irene Tatischeff, Gisele Tham, Nariyasu Mano

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Optically active lumazines (biolumazine, dictyolumazine, monalumazine, and neolumazine) are prepared from the corresponding pterins by enzymatic reaction, using pterin deaminase excreted by Dictyostelium discoideum. The fluorescence properties, circular dichroism spectra, and chromatographic behavior of these lumazines are studied. D‐ and L‐enantiomers of biolumazine, dictyolumazine, and monalumazine are separated using a chiral flavoprotein column. This column also separates the enantiomeric pterins of the threo form: monapterin and dictyopterin. However, the column does not separate the enantiomeric pterins of the erythro form: neopterin and biopterin. By coupling a reverse‐phase column to the flavoprotein column, the separation of pterins and lumazines in function of their hydrophobicity, as well as the separation of the diastereomers, is achieved. This coupled achiral/chiral high‐performance liquid chromatography method enables determination of the stereoconfiguration of natural lumazines by comparison with optically pure compounds. A lumazine derivative, present in the extracellular medium of Dictyostelium discoideum, is identified as D‐dictyolumazine, i.e., 6‐(D‐threo‐1,2‐dihydroxypropyl)‐lumazine. © 1994 Wiley‐Liss, Inc.

Original languageEnglish
Pages (from-to)564-571
Number of pages8
JournalChirality
Volume6
Issue number7
DOIs
Publication statusPublished - 1994
Externally publishedYes

Keywords

  • Dictyostelium discoideum
  • achiral/chiral chromatography
  • chiral HPLC
  • circular dichroism
  • flavoprotein column
  • fluorescence
  • pteridines
  • stereoconfiguration

ASJC Scopus subject areas

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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