Simultaneous determination of diastereoisomeric and enantiomeric impurities in SSS-octahydroindole-2-carboxylic acid by chiral high-performance liquid chromatography with pre-column derivatization

被引：8

作者：

Wang, Jin Zhao ^{[1
,2
]}

Zeng, Su ^{[2
]}

Hu, Gong Yun ^{[1
]}

Wang, Dan Hua ^{[1
]}

机构：

[1] Zhejiang Huahai Pharmaceut Co Ltd, Taizhou 317024, Zhejiang, Peoples R China

[2] Zhejiang Univ, Coll Pharmaceut Sci, Dept Pharmaceut Anal & Drug Metab, Hangzhou 310031, Zhejiang, Peoples R China

来源：

JOURNAL OF CHROMATOGRAPHY A | 2009年 / 1216卷 / 15期

关键词：

Octahydroindole-2-carboxylic acid; Diastereoisomers; Enantiomers; Pre-column derivatization; HUMAN PLASMA; RP-HPLC;

D O I：

10.1016/j.chroma.2009.01.053

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

SSS-Octahydroindole-2-carboxylic acid (SSS-Oic) is a key intermediate used in the synthesis of some angiotensin-converting enzyme (ACE) inhibitors. The separation of diastereoisomers and enantiomers of Oic was performed using a pre-column derivatization chiral HPLC method. Phenyl isothiocyanate (PITC) was used as the derivatization reagent. Three PITC derivatives of Oic stereoisomers were separated on an Ultron ES-OVM chiral column (150mm x 4.6mm, 5 mu m). Derivatization conditions such as reaction temperature, reaction time and derivatization reagent concentration were investigated. The chromatographic conditions for separation of the three PITC-Oic derivatives were optimized. The method was successfully applied in the diastereoisomeric and enantiomeric purity test of SSS-Oic. (C) 2009 Elsevier B.V. All rights reserved.

引用

页码：3044 / 3047

页数：4

共 10 条

[1] Determination of fluoxetine enantiomers in rat plasma by pre-column fluorescence derivatization and column-switching high-performance liquid chromatography [J].

Guo, XJ ;

Fukushima, T ;

Li, FM ;

Imai, K .

ANALYST, 2002, 127 (04) :480-484

[2] Determination of the stereoselectivity of chiral drug transport across Caco-2 cell monolayers [J].

He, Y ;

Zeng, S .

CHIRALITY, 2006, 18 (01) :64-69

[3]

Huang Y, 1998, BIOL PHARM BULL, V21, P156, DOI 10.1248/bpb.21.156

[4] Analysis of flurbiprofen, ketoprofen and etodolac enantiomers by pre-column derivatization RP-HPLC and application to drug-protein binding in human plasma [J].

Jin, Yin-Xiu ;

Tang, Yi-Hong ;

Zeng, Su .

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2008, 46 (05) :953-958

[5] Chiral HPLC for efficient resolution of enantiomers [J].

Okamoto, Yoshio ;

Ikai, Tomoyuki .

CHEMICAL SOCIETY REVIEWS, 2008, 37 (12) :2593-2608

[6] Chiral HPLC analysis of milnacipran and its FMOC-derivative on cellulose-based stationary phases [J].

Patti, Angela ;

Pedotti, Sonia ;

Sanfilippo, Claudia .

CHIRALITY, 2008, 20 (02) :63-68

[7] Chiral ligand-exchange chromatography for separation of three stereoisomers of octahydroindole-2-carboxylic acid [J].

Sun, SY ;

Jia, YZ ;

Zeng, N ;

Li, FM .

CHROMATOGRAPHIA, 2006, 63 (7-8) :331-335

[8]

TAKESHI F, 2003, J PHARM BIOMED ANAL, V30, P1655

[9] Stereoselective RP-HPLC determination of esmolol enantiomers in human plasma after pre-column derivatization [J].

Tang, YH ;

He, Y ;

Yao, TW ;

Zeng, S .

JOURNAL OF BIOCHEMICAL AND BIOPHYSICAL METHODS, 2004, 59 (02) :159-166

[10]

Vincent M, 1992, Drug Des Discov, V9, P11

← 1 →