Liquid chromatographic enantioseparation of the brominated flame retardant 2,3-dibromopropyl-2,4,6-tribromophenyl ether (DPTE) and enantiomer fractions in seal blubber.
Enantioselective analyses of the chiral brominated flame retardant 2,3-dibromopropyl-2,4,6-tribromophenyl ether (DPTE) are the focus of this work. High performance liquid chromatography (HPLC) equipped with a column that had a chiral stationary phase consisting of a modified cellulose derivative allowed for the fractionation of the enantiomers of DPTE. The enantiomeric excess was 98.2% for enantiomer 1 and 99% for enantiomer 2. Polarimetric measurements verified that the first eluting enantiomer originated from (-)-DPTE and the second peak originated from (+)-DPTE. Two gas chromatographic columns allowed for the direct enantioresolution of DPTE. The elution order of DPTE enantiomers was the same as observed in the chiral HPLC system ((-)-DPTE before (+)-DPTE). The best enantioseparation was achieved on a Chirasil-DEX CB column, which was used to analyze the enantiomer fractions of DPTE in blubber and brain samples of hooded seals (Cystophora cristata) and harp seals (Phoca groenlandica) from the Barents and Greenland Seas. Analyses were carried out by means of gas chromatography/electron capture negative ion mass spectrometry operated in the selected ion monitoring (GC/ECNI-MS-SIM) mode. In both matrices, only minute deviations from the racemate were observed (maximum +/-3% excess of (-)-DPTE). However, the samples from the Barents Sea were either racemic or showed a slight excess of (+)-DPTE (up to 2.5%), whereas all samples from the Greenland Sea contained a slight excess (up to 4%) of (-)-DPTE.
Institute of Food Chemistry, University of Hohenheim, Garbenstrasse 28, D-70599 Stuttgart, Germany. w-vetter@uni-hohenheim.de
Walter
W
Vetter
Roland von der
Rv
Recke
Patrizia
P
Ostrowicz
Natalie
N
Rosenfelder
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D003505:Cyclodextrins / Q000737:chemistry; D005411:Flame Retardants / Q000032:analysis* / Q000302:isolation & purification; D008401:Gas Chromatography-Mass Spectrometry; D006842:Hydrocarbons, Brominated / Q000032:analysis* / Q000302:isolation & purification; D046048:Seals, Earless; D012833:Siloxanes / Q000737:chemistry; D013237:Stereoisomerism
C547124:2,3-dibromopropyl-2,4,6-tribromophenyl ether; D003505:Cyclodextrins; D005411:Flame Retardants; D006842:Hydrocarbons, Brominated; D012833:Siloxanes; C090733:Chirasil-Dex