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Chiral amines as reagents for HPLC – MS enantioseparation of chiral carboxylic acids
Author(s) -
Tsutsui Haruhito,
Fujii Shinya,
Sakamoto Tasuku,
Min Jun Zhe,
Todoroki Kenichiro,
Toyo'oka Toshimasa
Publication year - 2012
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.201200091
Subject(s) - chemistry , chromatography , enantiomer , reagent , derivatization , chiral derivatizing agent , mass spectrometry , high performance liquid chromatography , pyrrolidine , electrospray ionization , electrospray , enantiomeric excess , enantioselective synthesis , chiral column chromatography , organic chemistry , catalysis
Mass spectrometry ( MS ) has become a popular analytical technique because of its high sensitivity and specificity. Therefore, the use of a chiral derivatization reagent for the MS detection seems to be efficient for the enantiomeric separation of racemates. However, the number of chiral reagents for the liquid chromatography ( LC )–tandem mass spectrometry ( MS/MS ) analysis is very limited. The applicability of commercially available chiral amines as the derivatization reagents for the enantiomeric separation of chiral carboxylic acids is reported in this paper by using non‐steroidal anti‐inflammatory drugs ( NSAID s), i.e. ibuprofen, flurbiprofen, and loxoprofen. The efficiency of the chiral reagents was evaluated in terms of tagging easiness, separation by reversed‐phase chromatography, and detection sensitivity by electrospray ionization ( ESI )– MS / MS . Among the tested eight chiral amines, i.e. ( R )‐(+)‐4‐(3‐aminopyrrolidin‐1‐yl)‐7‐( N,N ‐dimethylaminosulfonyl)‐2,1,3‐benzoxadiazole ( DBD‐AP y), ( S )‐(+)‐1‐(2‐pyrrolidinylmethyl)‐pyrrolidine ( PMP ), l ‐prolinamide, ( 3 R )‐(−)‐1‐benzyl‐3‐aminopyrrolidine, ( S )‐(+)‐1‐cyclohexyl‐ethylamine, ( 3 R )‐(+)‐3‐(trifluoroacetamido)‐pyrrolidine ( TFAP ), ( R )‐(−)‐1‐aminoindan ( AI ), and ( S )‐(+)‐tetrahydrofurfuryl‐amine, DBD‐AP y, PMP , AI , and TFAP could be used as the chiral reagents for the enantiomeric separation of the NSAID s. The R s values and the detection limits of the derivatives were in the range of 1.29–3.85 and 0.57–0.96 fmol, respectively. These four reagents were applied for the determination of the NSAID s in rat plasma.