Premium
Application of optically pure amines as chiral auxiliaries to develop trichloro‐ s ‐triazine‐based new chiral derivatizing reagents for reversed‐phase high‐performance liquid chromatographic enantioseparation of dl ‐selenomethionine
Author(s) -
Bhushan Ravi,
Lal Manohar
Publication year - 2013
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/bmc.2888
Subject(s) - chemistry , diastereomer , chromatography , reagent , trifluoroacetic acid , cyanuric chloride , detection limit , chiral derivatizing agent , triazine , amine gas treating , high performance liquid chromatography , acetonitrile , dansyl chloride , enantiomer , organic chemistry , derivatization , chiral column chromatography
( R )‐(+)‐naphthylethyl amine and ( S )‐(+)‐1‐benzyl‐3‐aminopyrrolidine were incorporated as chiral auxiliaries, by nucleophilic substitution of chlorine atoms, in cyanuric chloride (CC) or its 6‐butoxy derivative. There were obtained four new chiral derivatizing reagents (CDRs) as two dichloro and two monochloro triazine reagents. The CDRs so obtained were characterized and their optical purity was ascertained. Diastereomers of dl ‐selenomethionine were synthesized under microwave irradiation for 60 or 90 s (at 80% power of 800 W). Reversed‐phase high‐performance liquid chromatographic separation of diastereomers was carried out on a C 18 column using mixtures of acetonitrile with aqueous trifluoroacetic acid as mobile phase. The detection was made at 230 nm using a photodiode array detector. The separation behaviors in terms of retention times and resolutions were compared. The separation method was validated for limit of detection, linearity, accuracy, precision, and recovery. Copyright © 2013 John Wiley & Sons, Ltd.