Synthesis of fluorescent label, DBD-β-proline, and the resolution efficiency for chiral amines by reversed-phase chromatography

Biomedical Chromatography

Volumn 19, Issue 1, 2005, Pages 43-50

  Min, Jun Zhe ^a   Toyo'oka, Toshimasa ^a   Kato, Masaru ^a   Fukushima, Takeshi ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

Chiral resolution of amine; DBD proline; Diastereomer formation; Fluorescent labeling reagent; Reversed phase chromatography

Indexed keywords

AMINO ACIDS; CHROMATOGRAPHIC ANALYSIS; CHROMATOGRAPHY; DICHROISM; ENANTIOMERS; FLUORESCENCE; HEXANE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CHIRAL AMINES; CHIRAL RESOLUTION OF AMINE; CHIRAL RESOLUTIONS; CHIRAL STATIONARY PHASE; DBD-Β-PROLINE; DIASTEREOMER FORMATION; DIASTEREOMERS; FLUORESCENT LABELING REAGENT; REVERSED PHASE CHROMATOGRAPHY; SYNTHESISED;

AMINES;

1 (3 DIMETHYLAMINOPROPYL) 3 ETHYLCARBODIIMIDE; ALPHA METHYLBENZYLAMINE; AMINE; BENZENE DERIVATIVE; CARBOXYL GROUP; DIETHYLAMINE; ETHYLAMINE; FLUORESCENT DYE; PHENYLALANINE METHYL ESTER; PROLINE; PROLINE DERIVATIVE; PYRIDINE; PYRROLIDINE DERIVATIVE; REAGENT;

ANALYTICAL PARAMETERS; ARTICLE; CALIBRATION; CHEMICAL LABELING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DERIVATIZATION; DIASTEREOISOMER; ELECTROPHORETIC MOBILITY; ENANTIOMER; FLUORESCENCE ANALYSIS; FRACTIONATION; INTERMETHOD COMPARISON; LINEAR SYSTEM; RACEMIC MIXTURE; RACEMIZATION; REACTION ANALYSIS; REVERSED PHASE LIQUID CHROMATOGRAPHY; SEPARATION TECHNIQUE; SYNTHESIS;

EID: 14544298765     PISSN: 02693879     EISSN: None     Source Type: Journal    
DOI: 10.1002/bmc.414     Document Type: Article

References (19)

1. Al-Kindy S, Santa T, Fukushima T, Homma H and Imai K. Enatiomeric determination of amines by high-performance liquid chromatography using chiral fluorescent derivatization reagents. Biomedical Chromatography 1998; 12: 276-280.
2. Jin D, Nagakura K, Murofushi S, Miyahara T and Toyo'oka T. Total resolution of 17 DL-amino acids labelled with a fluorescent chiral reagent, R(-)-4-(3-Isothiocyanatopyrrolidin-1-yl)-7- (N,N-dimethylaminosulfonyl)-2,1,3-benzoxadiazole, by high-performance liquid chromatography. Journal of Chromatography A 1998; 822: 215-224.
3. Liu Y-M, Miao J-R and Toyo'oka T. Enantiomeric separation of di- and tripeptides with chiral fluorescence labelling reagents by liquid chromatography. Analytica Chimica Acta 1995; 314: 169-173.
4. Skidmore MW. Derivatization for Chromatographic Resolution of Optically Active Compounds, Handbook of Derivatization for Chromatography, 2nd edn, Blau K and Halket J (eds). Wiley: Chichester, 1993; 215-252.
5. Sun XX, Sun LZ and Aboul-Enein HY. Chiral derivatization reagents for drug enantioseparation by high-performance liquid chromatography based upon pre-column derivatization and formation of diastereomers: enantioselectivity and related structure. Biomedical Chromatography 2001; 15: 116-132.
6. Toyo'oka T. Recent progress in liquid chromatographic enantioseparation based upon diastereomer formation with fluorescent chiral derivatization reagents. Biomedical Chromatography 1996; 10: 265-277.
7. Toyo'oka T. Derivatization for Resolution of Chiral Compounds, Modern Derivatization Methods for Separation Sciences, Toyo'oka T (ed.). Wiley: Chichester, 1999; 217-289.
8. Toyo'oka T. Resolution of chiral drugs by liquid chromatography based upon diastereomer formation with chiral derivatization reagents. Journal of Biochemical and Biophysical Methods 2002a; 54: 25-56.
9. Toyo'oka T. Development of chiral derivatization reagents having benzofurazan (2,1,3-benzoxadiazole) fluorophore for HPLC analysis and their application to the sensitive dedtection of biologically important compounds. Bunseki Kagaku 2002b; 51: 339-358.
10. Toyo'oka T and Liu Y-M. Development of optically active fluorescent 'Edman-type' reagents. Analyst 1995a; 120: 385-390.
11. Toyo'oka T and Liu Y-M. Resolution of amino acid enantiomers by high-performance liquid chromatography with fluorescent chiral Edman reagents. Journal of Chromatography A 1995b; 689: 23-30.
12. Toyo'oka T, Suzuki T, Saito Y, Uzu S and Imai K. Evaluation of benzofurazan derivatives as fluorogenic reagents for thiols and amines using high-performance liquid chromatography. Analyst 1989a; 114 1233-1240.
13. Toyo'oka T, Suzuki T, Saito Y, Uzu S and Imai K. 4-(N,N Dimethylaminosulfonyl)-7-fluoro-2,1,3-benzoxadiazole: A new fluorogenic reagents for thiols. Analyst 1989b; 114: 413-419.
14. Toyo'oka T, Ishibashi M and Terao T. Resolution of carboxylic acid enantiomers by high-performance liquid chromatography with peroxyoxalate chemiluminescence detection. Journal of Chromatography 1992a; 627: 75-86.
15. Toyo'oka T, Ishibashi M and Terao T. Resolution of carboxylic acid enantiomers by high-performance liquid chromatography with highly sensitive laser-induced fluorescence detection. Journal of Chromatography 1992b; 625: 357-361.
16. Toyo'oka T, Ishibashi M and Terao T. Further studies for the resolution of carboxylic acid enantiomers by high-performance liquid chromatography with fluorescence and laser-induced fluorescence detection. Analytica Chimica Acta 1993a; 278: 71-81.
17. Toyo'oka T, Ishibashi M, Terao T and Imai K. 4-(N,N Dimethylaminosulfonyl)-7-(2-chroloformylpyrrolidin-1-yl) -2,1,3-benzoxadiazole: Novel fluorescent chiral derivatization reagents for the resolution of alcohol enantiomers by high-performance liquid chromatography. Analyst 1993b; 118: 759-763.
18. Toyo'oka T, Liu Y-M, Jinno H, Hanioka N, Ando M and Imai K. Chiral separation of amines by high-performance liquid chromatography after tagging with 4-(N,N dimethylaminosulfonyl)-7-(2-chloroformylpyrrolidin-1-yl) -2,1,3-benzoxadiazole. Biomedical Chromatography 1994a; 8: 85-89.
19. Toyo'oka T, Liu Y-M, Hanioka N, Jinno H and Ando M. Determination of hydroxuls and amines, labeled with 4-(N,N dimethylaminosulfonyl)-7-(2-chloroformylpyrrolidin-1-yl) -2,1,3-benzoxadiazole, by high-performance liquid chromatography with fluorescence and laser-induced fluorescence detection. Analytica Chimica Acta 1994b; 285: 343-351.