The effect of acidic and basic additives on the enantioseparation of basic drugs using polysaccharide-based chiral stationary phases

Chirality

Volumn 18, Issue 7, 2006, Pages 519-530

  Ye, Yun K ^a   Stringham, Rodger W ^a,b  

^a BRISTOL MYERS SQUIBB   (United States)

^b Chiral Technologies Inc   (United States)

Author keywords

Drugs; Enantioseparation; HPLC; Mobile phase additives

Indexed keywords

2 PROPANOL; ALPRENOLOL; ATENOLOL; BUTYLAMINE; CLENBUTEROL; ESYLIC ACID; METOPROLOL; ORCIPRENALINE; OXPRENOLOL; PINDOLOL; POLYSACCHARIDE; PROPRANOLOL; SULFONIC ACID DERIVATIVE; TERBUTALINE; UNCLASSIFIED DRUG;

ACIDITY; CHIRALITY; CONFERENCE PAPER; DRUG DETERMINATION; DRUG PURITY; DRUG STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; SENSITIVITY AND SPECIFICITY; ULTRAVIOLET SPECTROSCOPY;

2-PROPANOL; ACIDS; ALKANESULFONATES; CHROMATOGRAPHY, LIQUID; HYDROGEN BONDING; MOLECULAR STRUCTURE; PHARMACEUTICAL PREPARATIONS; POLYSACCHARIDES; SENSITIVITY AND SPECIFICITY; STEREOISOMERISM;

EID: 33745372935     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20287     Document Type: Conference Paper

References (26)

1. Yashima E, Yamamoto C, Okamoto Y. Polysaccharide-based chiral LC columns. Synlett 1998;4:344-360.
2. Okamoto Y, Kaida Y. Resolution by high-performance liquid chromatography using polysaccharide carbamates and benzoates as chiral stationary. J Chromatogr A 1994;666:403-419.
3. Okamoto Y, Yashima E. Polysaccharide derivatives for chromatographic separation of enantiomers. Angew Chem Int Ed 1998;37:1020-1043.
4. Yashima E. Polysaccharide-based chiral stationary phases for high-performance liquid chromatographic enantioseparation. J Chromatogr A 2001;906:105-125.
5. Tachibana K, Ohnishi A. Reversed-phase liquid chromatographic separation of enantiomers on polysaccharide type chiral stationary phases. J Chromatogr A 2001;906:127-154.
6. Yashima K, Okamoto Y. Chiral discrimination on polysaccharides derivatives. Bull Chem Soc Jpn 1995;68:3289-3307.
7. Yashima K, Okamoto Y. Chiral discrimination on polysaccharides derivatives. Bull Chem Soc Jpn 1995;68:3289-3307.
8. Reta M, Carr P. Comparative study of divalent metals and amines as silanol-blocking agents in reversed-phase liquid chromatography. J Chromatogr A 1999;855:121-127.
9. Vervoort R, Maris F, Hindriks H. Comparison of high-performance liquid chromatographic methods for the analysis of basic drugs. J Chromatogr A 1992;623:207-220.
10. Melander W, Stovekeen J, Horvàth C. Mobile phase effects in reversed-phase chromatography: II. Acidic amine phosphate buffers as eluents. J Chromatogr A 1979;185:111-127.
11. Okamoto Y, Aburatani R, Kaida Y, Hatada K, Inotsume N, Nakano M. Direct chromatographic separation of 2-arylpropionic acid enantiomers using tris(3,5-dimethylphenylcarbamate)s of cellulose and amylose as chiral stationary phases. Chirality 1989;1:239-242.
12. Okamoto Y, Aburatani R, Hatada K. Direct optical resolution of abscisic acid by high performance liquid chromatography on cellulose tris(3,5- dimethylphenylcarbamate). J Chromatogr 1988;448:454-455.
13. Okamoto Y, Aburatani R, Kaida Y, Hatada K. Direct optical resolution of carboxylic acids by chiral HPLC on tris(3,5-dimethylphenylcarbamate)s of cellulose and amylose. Chem Lett 1988;17:1125-1128.
14. Aboul-Enein H, Islam M. Direct separation and optimization of timolol enantiomers on a cellulose tris-3,5-dimethylphenylcarbamate high-performance liquid chromatographic chiral stationary. J Chromatogr 1990;511:109-114.
15. Okamato Y, Aburatani K, Hatada K. Chromatographic resolution: XXI. Direct optical resolution of abscisic acid by high-performance liquid chromatography on cellulose tris(3,5-dimethylphenylcarbamate). J Chromatogr 1988;448:454-455.
16. Krstulovic A, Fouchet M, Burke J, Gillet G, Durand A. Direct enantiomeric separation of betaxolol with applications to analysis of bulk drug and biological samples. J Chromatogr 1988;452:477-483.
17. Tang Y. Significance of mobile phase composition in enantioseparation of chiral drugs by HPLC on a cellulose-based chiral stationary phase. Chirality 1996;8:136-142.
18. Tang Y, Zielinski W, Bigott H. Separation of nicotine and nornicotine enantiomers via normal phase HPLC on derivatized cellulose chiral stationary phases. Chirality 1998;10:364-369.
19. Blackwell J. Effect of acidic mobile phase additives on chiral selectivity for phenylalamine analogs using subcritical fluid chromatography. Chirality 1999;11:91-97.
20. Ye YK, Stringham RW. Effect of mobile phase acidic additives on enantioselectivity for phenylalanine analogs. J Chromatogr A 2001;927:47-52.
21. Ye YK, Stringham RW. Effect of mobile phase amine additives on enantioselectivity for phenylalanine analogs. J Chromatogr A 2001;927:53-60.
22. Ye YK, Lord B, Stringham RW. Memory effect of mobile phase additives in chiral separations on a Chiralpak AD column. J Chromatogr A 2002;945:139-146.
23. Ye YK, Lord B, Yin L, Stringham RW. Enantioseparation of amino acids on a polysaccharide-based chiral stationary phase. J Chromatogr A 2002;945:147-159.
24. Ye YK, Lynam G, Stringham RW. Effect of amine mobile phase additives on chiral subcritical fluid chromatography using polysaccharide stationary phases. J Chromatogr A 2004;1041:211-217.
25. Ye YK, Stringham RW, Wirth MJ. Origin of enhanced chiral selectivity by acidic additives for a polysaccharide-based stationary phase. J Chromatogr A 2004;1057:75-82.
26. Stringham RW, Lynam KG, Lord BS. Memory effect of diethylamine mobile phase additive on chiral separations on polysaccharide stationary phases. Chirality 2004;16:493-498.