Molecular modeling of enantiomeric resolution of methylphenidate on cellulose tris benzoate chiral stationary phase

被引:16
作者
Aboul-Enein, HY
Ali, M
Laguerre, M
Felix, G
机构
[1] King Faisal Specialist Hosp & Res Ctr, Biol & Med Res Dept MBC03, Pharmaceut Anal Lab, Riyadh 11211, Saudi Arabia
[2] ENSCPB, Ecole Polytech, IECB, F-33607 Pessac, France
[3] ENSCPB, F-33402 Talence, France
关键词
D O I
10.1081/JLC-120014946
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
The enantiomeric resolution of (+/-)-threo methylphenidate (MPH) (Ritalin(R)) has been achieved on Chiralcel OB column using the mobile phase hexane-ethanol-methanol-trifluoroacetic acid (480:9.75:9.75 :0.5, v/v/v/v), containing benzoic acid and phenol as mobile phase additives. Ultraviolet detection was carried out at 230 nm. Molecular modeling was carried out to explain the chiral resolution mechanism of MPH enantiomers.
引用
收藏
页码:2739 / 2748
页数:10
相关论文
共 22 条
[11]  
KLEIN RG, 1995, ARCH GEN PSYCHIAT, V52, P429
[12]   Methylphenidate treatment for cocaine abusers with adult attention-deficit/hyperactivity disorder: A pilot study [J].
Levin, FR ;
Evans, SM ;
McDowell, DM ;
Kleber, HD .
JOURNAL OF CLINICAL PSYCHIATRY, 1998, 59 (06) :300-305
[13]  
MAXWELL RA, 1970, J PHARMACOL EXP THER, V173, P158
[14]   MACROMODEL - AN INTEGRATED SOFTWARE SYSTEM FOR MODELING ORGANIC AND BIOORGANIC MOLECULES USING MOLECULAR MECHANICS [J].
MOHAMADI, F ;
RICHARDS, NGJ ;
GUIDA, WC ;
LISKAMP, R ;
LIPTON, M ;
CAUFIELD, C ;
CHANG, G ;
HENDRICKSON, T ;
STILL, WC .
JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (04) :440-467
[15]  
SPENCER T, 1995, ARCH GEN PSYCHIAT, V52, P434
[16]  
SRINIVAS NR, 1987, J PHARMACOL EXP THER, V241, P300
[17]   SEMIANALYTICAL TREATMENT OF SOLVATION FOR MOLECULAR MECHANICS AND DYNAMICS [J].
STILL, WC ;
TEMPCZYK, A ;
HAWLEY, RC ;
HENDRICKSON, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (16) :6127-6129
[18]   A LEAP-FROG ALGORITHM FOR STOCHASTIC DYNAMICS [J].
Van Gunsteren, W. F. ;
Berendsen, H. J. C. .
MOLECULAR SIMULATION, 1988, 1 (03) :173-185
[19]   RESOLUTION OF ENANTIOMERIC AMIDES ON A CELLULOSE-BASED CHIRAL STATIONARY PHASE - STERIC AND ELECTRONIC EFFECTS [J].
WAINER, IW ;
ALEMBIK, MC .
JOURNAL OF CHROMATOGRAPHY, 1986, 358 (01) :85-93
[20]   RESOLUTION OF ENANTIOMERIC AROMATIC ALCOHOLS ON A CELLULOSE TRIBENZOATE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY CHIRAL STATIONARY PHASE - A PROPOSED CHIRAL RECOGNITION MECHANISM [J].
WAINER, IW ;
STIFFIN, RM ;
SHIBATA, T .
JOURNAL OF CHROMATOGRAPHY, 1987, 411 :139-151