Indirect enantiomeric separation of 2-arylpropionic acids and structurally related compounds by reversed phase HPLC

被引：13

作者：

Thomason, MJ ^{[1
]}

Hung, YF ^{[1
]}

RhysWilliams, W ^{[1
]}

Hanlon, GW ^{[1
]}

Lloyd, AW ^{[1
]}

机构：

[1] UNIV BRIGHTON,DEPT PHARM,MICROBIAL BIOTRANSFORMAT GRP,BRIGHTON BN2 4GJ,E SUSSEX,ENGLAND

来源：

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS | 1997年 / 15卷 / 11期

基金：

英国惠康基金;

关键词：

reversed phase HPLC; indirect enantiomeric separation; microbial chiral inversion; 2-arylpropionic acid non-steroidal anti-inflammatory drugs;

D O I：

10.1016/S0731-7085(96)01979-6

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

A reversed-phase high-performance liquid chromatographic method, using an organic modifier-phosphate buffered mobile phase, for the determination of the enantiomeric composition of 2-arylpropionic acids and other structurally related compounds in microbial media is described. The method is based on the resolution of diastereoisomeric amides formed from the reaction of the arylpropionic acid with either (-)-(S)-alpha-methylbenzylamine or (-)-(S)-1-(naphthen-1-yl)ethylamine in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide HCl and 1-hydroxybenzotriazole and incorporating an internal standard. The addition of sodium pentanesulphonate to the mobile phase as an ion-pairing agent was necessary to remove unreacted amine to avoid rapid column deterioration. The method provides an efficient, rapid and reproducible means of monitoring the microbial chiral inversion of 2-arylpropionic acids and other structurally related molecules. (C) 1997 Elsevier Science B.V.

引用

页码：1765 / 1774

页数：10

共 24 条

[11]

KOOLOOBANDI A, 1992, THESIS CNAA

[12]

KOOLOOBANDI A, 1993, J PHARM PHARM S, V45, pP96

[13]

MAYER JM, 1990, ACTA PHARM NORDICA, V2, P197

[14] PHARMACOLOGICAL ASPECTS OF CHIRAL NONSTEROIDAL ANTIINFLAMMATORY DRUGS [J].

MULLER, N ;

PAYAN, E ;

LAPICQUE, F ;

BANNWARTH, B ;

NETTER, P .

FUNDAMENTAL & CLINICAL PHARMACOLOGY, 1990, 4 (06) :617-634

[15]

RHYSWILLIAMS W, 1995, P 4 ANN UKAPS C, P72

[16]

Shen T.J., 1981, BURGERS MED CHEM 3, P1205

[17] STEREOSELECTIVE GAS-CHROMATOGRAPHIC ANALYSIS OF ETODOLAC ENANTIOMERS IN HUMAN-PLASMA AND URINE [J].

SINGH, NN ;

JAMALI, F ;

PASUTTO, FM ;

COUTTS, RT ;

RUSSELL, AS .

JOURNAL OF CHROMATOGRAPHY, 1986, 382 :331-337

[18] DETERMINATION OF THE (+)-ENANTIOMERS AND (-)-ENANTIOMERS OF PIRPROFEN IN HUMAN-PLASMA BY HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].

SIOUFI, A ;

COLUSSI, D ;

MARFIL, F ;

DUBOIS, JP .

JOURNAL OF CHROMATOGRAPHY-BIOMEDICAL APPLICATIONS, 1987, 414 (01) :131-137

[19]

THOMASON MJ, 1994, J PHARM PHARMACOL, V46, pP22

[20]

THOMASON MJ, 1995, J PHARM PHARM S, V47, pP6

← 1 2 3 →