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Enantiomeric separation and detection by high‐performance liquid chromatography‐mass spectrometry of 2‐arylpropionic acids derivatized with benzofurazan fluorescent reagents
Author(s) -
Santa Tomofumi,
Luo Jinli,
Lim ChangKee,
Imai Kuzuhiro
Publication year - 1998
Publication title -
biomedical chromatography
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.4
H-Index - 65
eISSN - 1099-0801
pISSN - 0269-3879
DOI - 10.1002/(sici)1099-0801(199803/04)12:2<73::aid-bmc725>3.0.co;2-b
Subject(s) - chemistry , chromatography , derivatization , reagent , mass spectrometry , electrospray ionization , enantiomer , high performance liquid chromatography , diastereomer , electrospray , organic chemistry
Abstract The enantiomneric separation and the detection of 2‐arylpropionic acids after derivatization with the fluorescent reagents with a benzofurazan structure, ( S )‐(+)‐4‐( N,N ‐dimethylaminosulphonyl)‐7‐(3‐aminopyrrolidin‐1‐yl)‐2,1,3‐benzoxadiazole (( S )‐DBD‐Apy), (R)‐(‐)‐4‐nitro‐7‐(3‐aminopyrrolidin‐1‐yl)‐2,1,3‐benzoxadiazole (( R )‐NBD‐Apy), 4‐ N,N ‐dimethylaminosulphonyl‐7‐piperazino‐2,1,3‐benzoxadiazole (DBD‐PZ) and N ‐hydrazinoformylmethyl‐ N ‐methylamino‐4,4‐ N,N ‐dimethylaminosulphonyl‐2,1,3‐benzoxadiazole (DBD‐CO‐Hz) by high‐performance liquid chromatography (HPLC) and electrospray ionization mass spectrometry (ESI‐MS) were examined. The diastereomeric derivatization with ( S )‐DBD‐Apy or ( R )‐NBD‐Apy and the separation on the reversed phase column afforded the high sensitivity. The separation on chiral stationary phase after non‐chiral derivatization with DBD‐PZ or DBD‐CO‐Hz provided less sensitivity. The signal‐to‐noise ratio of ( S )‐DBD‐Apy‐( S )‐ketoprofen of 200:1 was observed for 12.5 picomole (pmol) injection and selected ion monitoring (SIM) of the quasi‐molecular ion after splitting 1:7 before entering into the electrospray ion sources. As a result, the usefulness of these reagents for MS detection has been demonstrated. © 1998 John Wiley & Sons, Ltd.