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Chiral separation of amines by high‐performance liquid chromatography after tagging with 4‐( N , N ‐dimethylaminosulphonyl)‐7‐(2‐chloroformylpyrrolidin‐1‐yl)‐2,1,3‐benzoxadiazole
Author(s) -
Toyo'oka Toshimasa,
Liu YiMing,
Jinno Hideto,
Hanioka Nobumitsu,
Ando Masanori,
Imai Kazuhiro
Publication year - 1994
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.1130080208
Subject(s) - chemistry , diastereomer , reagent , enantiomer , derivatization , chromatography , ethylamine , elution , pyridine , column chromatography , high performance liquid chromatography , organic chemistry
Chiral tagging reagents, 4‐( N , N ‐dimethylaminosulphonyl)‐7‐(2‐chloroformylpyrrolidin‐1‐yl)‐2,1,3‐benzoxadiazole ( R (+)‐DBD‐Pro‐COCl and S (−)‐DBD‐Pro‐COCI), react with mirror image enantiomers of amines to produce corresponding diastereomers in the presence of pyridine as a catalyst. The maximal excitation and emission wavelengths of the resulting diastereomers were ca. 450 nm and 560 nm, respectively. The diastereomers derived from some aliphatic amines were resolved by a reversed‐phase chromatography with water–acetonitrile or normal‐phase chromatography with n ‐hexane–ethyl acetate as the eluent. The reactivities of both enantiomers of DBD‐Pro‐COCI to chiral amines were almost comparable, whereas a slight difference of fluorescence intensity was observed with S (−)‐DBD‐Pro‐COCI. When S (−)‐DBD‐Pro‐COCI was used as the derivatization reagent, amines corresponding to S ‐configuration were eluted faster than R ‐configuration. The opposite elution order was obtained with the use of R (+)‐DBD‐Pro‐COCI, instead of S (−)‐DBD‐Pro‐COCI. The R s values obtained from 1‐cyclohexylethylamine (CEA) having aliphatic ring structure was larger than those of amines (1‐(1‐naphtyl)ethylamine (NEA) and 1‐phenylethylamine (PEA)) having aromatic ring structures.