Determination of the enantiomeric purity of the phytoalexins spirobrassinins by 1H NMR using chiral solvation

被引:27
作者
Pedras, MSC [1 ]
Hossain, M [1 ]
Sarwar, MG [1 ]
Montaut, S [1 ]
机构
[1] Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
spirobrassinin; 1-methoxyspirobrassinin; enantiomeric purity; chiral solvation;
D O I
10.1016/j.bmcl.2004.09.014
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A simple and inexpensive method for enantiomeric discrimination of the phytoalexins spirobrassinin (1), 1-methoxyspirobrassinin (2) and synthetic analog 1-methylspirobrassinin (6) using the chiral solvating agent 2,2,2-trifluoro-1-(9-anthryl)ethanol in C6D6 is described. Using this method the enantiomeric composition of each sample can be determined accurately by H-1 NMR and the compounds can be recovered readily by chromatography. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5469 / 5471
页数:3
相关论文
共 50 条
[21]   HPLC Determination of Enantiomeric Purity of PF-04136309 Based on a Chiral Stationary Phase [J].
Zuo, Zeping ;
Hu, Mingxing ;
Chen, Miaomiao ;
Chen, Xiuli ;
Yang, Fangfang ;
Zeng, Chenjuan ;
Zhao, Yinglan ;
Zhang, Yiwen .
CHROMATOGRAPHIA, 2015, 78 (7-8) :579-583
[22]   HPLC Determination of Enantiomeric Purity of PF-04136309 Based on a Chiral Stationary Phase [J].
Zeping Zuo ;
Mingxing Hu ;
Miaomiao Chen ;
Xiuli Chen ;
Fangfang Yang ;
Chenjuan Zeng ;
Yinglan Zhao ;
Yiwen Zhang .
Chromatographia, 2015, 78 :579-583
[23]   Simple Chiral Derivatization Protocols for 1H NMR and 19F NMR Spectroscopic Analysis of the Enantiopurity of Chiral Diols [J].
Yeste, Sonia Lozano ;
Powell, Magdalena E. ;
Bull, Steven D. ;
James, Tony D. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (01) :427-430
[24]   Using NMR spectroscopic methods to determine enantiomeric purity and assign absolute stereochemistry [J].
Wenzel, Thomas J. ;
Chisholm, Cora D. .
PROGRESS IN NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY, 2011, 59 (01) :1-63
[25]   N-COUMARINYL-L-PROLINE, A NOVEL CHIRAL DERIVATIZING AGENT FOR H-1-NMR DETERMINATION OF ENANTIOMERIC PURITIES OF ALCOHOLS AND AMINES [J].
NAGASAWA, K ;
YAMASHITA, A ;
KATOH, S ;
ITO, K ;
WADA, K .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1995, 43 (02) :344-346
[26]   HPLC ENANTIOSEPARATION OF THE ALKALOID CANADINE AND DETERMINATION OF ENANTIOMERIC PURITY WITH CHIRAL/PHOTOMETRIC AND ACHIRAL/POLARIMETRIC DETECTION [J].
Garcia Sanchez, Francisco ;
Navas Diaz, Aurora ;
Medina Lama, Ignacio ;
Aguilar, Alfonso ;
Algarra, Manuel .
JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES, 2014, 37 (01) :26-38
[27]   A validated chiral LC method for the determination of enantiomeric purity of pemetrexed disodium on an amylose-based chiral stationary phase [J].
Ramulu, K. ;
Rao, B. M. ;
Madhavan, P. ;
Devi, M. Lalitha ;
Srinivasu, M. K. ;
Chandrasekhar, K. B. .
CHROMATOGRAPHIA, 2007, 65 (3-4) :249-252
[28]   A Validated Chiral LC Method for the Determination of Enantiomeric Purity of Pemetrexed Disodium on an Amylose-Based Chiral Stationary Phase [J].
K. Ramulu ;
B. M. Rao ;
P. Madhavan ;
M. Lalitha Devi ;
M. K. Srinivasu ;
K. B. Chandrasekhar .
Chromatographia, 2007, 65 :249-252
[29]   Direct enantiomeric separation and determination of enantiomeric purity of methoxytetrahydro-naphthalene derivatives and melatonin ligands by HPLC using RSP-β-cyclodextrin as chiral stationary phase [J].
Lipka, E. ;
Bonte, J. -P. ;
Vaccher, C. .
JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES, 2006, 29 (09) :1235-1245
[30]   Development and validation of TLC-densitometric method for resolution and determination of enantiomeric purity of ropivacaine, using different cyclodextrins as chiral selector [J].
Taha, Elharn A. .
CURRENT PHARMACEUTICAL ANALYSIS, 2007, 3 (04) :273-277