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Chiral lumazines: preparation, properties, enantiomeric separation
R Klein1, I Tatischeff, G Tham
1Laboratoire de Physique et Chimie Biomoléculaires (UA 198, CNRS et Université P. et M. Curie), Institut Curie, Paris, France.
Chirality
|January 1, 1994
Summary
Optically active lumazines were synthesized and separated using a novel chiral chromatography method. This technique allows for the determination of stereoconfiguration in natural lumazines, identifying D-dictyolumazine in Dictyostelium discoideum.
Area of Science:
- Biochemistry
- Analytical Chemistry
- Chromatography
Background:
- Optically active lumazines are biologically significant compounds.
- Enzymatic synthesis offers a route to optically active lumazines from pterins.
- Dictyostelium discoideum excretes pterin deaminase, an enzyme relevant to lumazine synthesis.
Purpose of the Study:
- To synthesize optically active lumazines from corresponding pterins.
- To investigate the fluorescence properties, circular dichroism spectra, and chromatographic behavior of these lumazines.
- To develop a method for determining the stereoconfiguration of natural lumazines.
Main Methods:
- Enzymatic preparation of lumazines using pterin deaminase from Dictyostelium discoideum.
- Chiral flavoprotein column chromatography for enantiomer separation.
- Coupled achiral/chiral high-performance liquid chromatography (HPLC) for enhanced separation.
- Analysis of fluorescence properties and circular dichroism spectra.
Main Results:
- D- and L-enantiomers of biolumazine, dictyolumazine, and monalumazine were separated using a chiral flavoprotein column.
- Enantiomeric pterins of the threo form (monapterin, dictyopterin) were separated, but not the erythro form (neopterin, biopterin).
- A coupled HPLC method achieved separation based on hydrophobicity and diastereomers.
- D-dictyolumazine (6-(D-threo-1,2-dihydroxypropyl)-lumazine) was identified in Dictyostelium discoideum extracellular medium.
Conclusions:
- A robust HPLC method combining chiral and achiral columns enables stereochemical determination of lumazines.
- The method is effective for separating enantiomers and diastereomers of pterins and lumazines.
- The extracellular lumazine derivative from Dictyostelium discoideum is confirmed as D-dictyolumazine.