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R(−)-4-(3-Isothiocyanatopyrrolidin-1-yl)-7-(N,N-dimethylaminosulfonyl)-2,1,3-benzoxadiazole, a fluorescent chiral tagging reagent: sensitive resolution of chiral amines and amino acids by reversed-phase liquid chromatography by Toshimasa Toyo'oka; Dongri Jin; Nobue Tomoi; Tomoyuki Oe; Hidenori Hiranuma is a Chemistry article available to read on EtoBox.

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## Abstract The usefulness of __R__(−)‐4‐(3‐isothiocyanatopyrrolidin‐1‐yl)‐7‐(__N,N__‐dimethylaminosulfonyl)‐2,1,3‐benzoxadiazole [__R__(−)‐DBD‐PyNCS], a fluorescent chiral tagging reagent, for the determination of racemic amines and amino acids, was studied. The reagent reacted with β‐blockers selected as representative secondary amines to produce corresponding fluorescent diastereomers (excitation at 460 nm and emission at 550 nm). The yields of the derivatization reaction were dependent on the stereostructure arround the NH group in β‐blockers. The resulting diastereomers were completely separated with single chromatographic run using linear gradient elutions by reversed‐phase chromatography. __R__(−)‐DBD‐PyNCS was also applied to the determination of DL‐amino acid, considered to be one of the primary amines, in human urine and foodstuffs. DL‐amino acids tested equally reacted with the reagent, and the thiocarbamoyl derivatives were separated with an ODS column. The epimerization during the derivatization reaction was negligible judging from the resolution of opposite diastereomers on the chromatogram. The occurence of D‐amino acids (D‐Ala, D‐Ser, D‐Asp and/or D‐Glu) was identif

Who reads R(−)-4-(3-Isothiocyanatopyrrolidin-1-yl)-7-(N,N-dimethylaminosulfonyl)-2,1,3-benzoxadiazole, a fluorescent chiral tagging reagent: sensitive resolution of chiral amines and amino acids by reversed-phase liquid chromatography?

Author

Toshimasa Toyo'oka; Dongri Jin; Nobue Tomoi; Tomoyuki Oe; Hidenori Hiranuma

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Inc.; Wiley (ISSN 0269-3879)

Published

2001

Language

EN

Field

Chemistry (Physical Sciences)