TY - JOUR
T1 - Ferrocene derivatization reagents for optical resolution of carboxylic acids by high-performance liquid chromatography with electrochemical detection
AU - Shimada, Kazutake
AU - Haniuda, Emi
AU - Oe, Tomoyuki
AU - Nambara, Toshio
N1 - Funding Information:
The authors are indebted to Miss C. Sakayori for her technical assistance. We also express our thanks to the staff of the central analytical laboratory of this Institute for elemental analyses and spectral measurements. This work was supported in part by a grant from the Ministry of Education, Science and Culture of Japan.
PY - 1987/10/1
Y1 - 1987/10/1
N2 - New derivatization methods using chiral ferrocene reagents have been developed for the optical resolution of carboxylic acids by high-performance liquid chromatography with electrochemical detection. Two chiral derivatization reagents, 1-ferrocenylethylamine and 1-ferrocenylpropylamine, were readily prepared from acetyl ferrocene and propionylferrocene in two steps, respectively. Condensation of carboxylic acids with the chiral reagent was effected in the presence of water-soluble carbodiimide and 1-hydroxybenzotriazole. The diastereomeric amides formed from N-acetylamino acid and α-arylpropionic acid enantiomers were efficiently resolved by reversed-phase chromatography and showed the satisfactory sensitivity at +0.45 V vs. an Ag/AgCl reference electrode with a detection limit of 0.5 pmole (S/N=5).
AB - New derivatization methods using chiral ferrocene reagents have been developed for the optical resolution of carboxylic acids by high-performance liquid chromatography with electrochemical detection. Two chiral derivatization reagents, 1-ferrocenylethylamine and 1-ferrocenylpropylamine, were readily prepared from acetyl ferrocene and propionylferrocene in two steps, respectively. Condensation of carboxylic acids with the chiral reagent was effected in the presence of water-soluble carbodiimide and 1-hydroxybenzotriazole. The diastereomeric amides formed from N-acetylamino acid and α-arylpropionic acid enantiomers were efficiently resolved by reversed-phase chromatography and showed the satisfactory sensitivity at +0.45 V vs. an Ag/AgCl reference electrode with a detection limit of 0.5 pmole (S/N=5).
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U2 - 10.1080/01483918708068304
DO - 10.1080/01483918708068304
M3 - Article
AN - SCOPUS:0023567959
SN - 0148-3919
VL - 10
SP - 3161
EP - 3172
JO - Journal of Liquid Chromatography
JF - Journal of Liquid Chromatography
IS - 14
ER -