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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.
Biomed Chromatogr. 1994 Mar-Apr; 8(2):85-9.BC

Abstract

Chiral tagging reagents, 4-(N,N-dimethylaminosulphonyl)-7-(2-chloroformylpyrrolidin-1 -yl)-2,1,3- benzoxadiazole (R(+)-DBD-Pro-COCl and S(-)-DBD-Pro-COCl), 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-COCl to chiral amines were almost comparable, whereas a slight difference of fluorescence intensity was observed with S(-)-DBD-Pro-COCl. When (S-)-DBD-Pro-COCl 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-COCl, instead of S(-)-DBD-Pro-COCl. The Rs values obtained from 1-cyclohexylethylamine (CEA) having aliphatic ring structure was larger than those of amines (1-(1-naphthyl)ethylamine (NEA) and 1-phenylethylamine (PEA)) having aromatic ring structures.

Authors+Show Affiliations

Toyo'oka T
Division of Environmental Chemistry, National Institute of Health Sciences (NIHS), Tokyo, Japan.
Liu YM
No affiliation info available
Jinno H
No affiliation info available
Hanioka N
No affiliation info available
Ando M
No affiliation info available
Imai K
No affiliation info available

MeSH

AminesChromatography, High Pressure LiquidIndicators and ReagentsOxadiazolesPyrrolidinesStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

8044027

Citation

Toyo'oka, T, et al. "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." Biomedical Chromatography : BMC, vol. 8, no. 2, 1994, pp. 85-9.
Toyo'oka T, Liu YM, Jinno H, et al. 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. Biomed Chromatogr. 1994;8(2):85-9.
Toyo'oka, T., Liu, Y. M., Jinno, H., Hanioka, N., Ando, M., & Imai, K. (1994). 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. Biomedical Chromatography : BMC, 8(2), 85-9.
Toyo'oka T, et al. 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. Biomed Chromatogr. 1994 Mar-Apr;8(2):85-9. PubMed PMID: 8044027.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 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. AU - Toyo'oka,T, AU - Liu,Y M, AU - Jinno,H, AU - Hanioka,N, AU - Ando,M, AU - Imai,K, PY - 1994/3/1/pubmed PY - 1994/3/1/medline PY - 1994/3/1/entrez SP - 85 EP - 9 JF - Biomedical chromatography : BMC JO - Biomed Chromatogr VL - 8 IS - 2 N2 - Chiral tagging reagents, 4-(N,N-dimethylaminosulphonyl)-7-(2-chloroformylpyrrolidin-1 -yl)-2,1,3- benzoxadiazole (R(+)-DBD-Pro-COCl and S(-)-DBD-Pro-COCl), 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-COCl to chiral amines were almost comparable, whereas a slight difference of fluorescence intensity was observed with S(-)-DBD-Pro-COCl. When (S-)-DBD-Pro-COCl 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-COCl, instead of S(-)-DBD-Pro-COCl. The Rs values obtained from 1-cyclohexylethylamine (CEA) having aliphatic ring structure was larger than those of amines (1-(1-naphthyl)ethylamine (NEA) and 1-phenylethylamine (PEA)) having aromatic ring structures. SN - 0269-3879 UR - https://www.unboundmedicine.com/medline/citation/8044027/Chiral_separation_of_amines_by_high_performance_liquid_chromatography_after_tagging_with_4__NN_dimethylaminosulphonyl__7__2_chloroformylpyrrolidin_1_yl___213_benzoxadiazole_ L2 - https://doi.org/10.1002/bmc.1130080208 DB - PRIME DP - Unbound Medicine ER -

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