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
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2004年 / 14卷 / 22期
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
[41]   Resolution, determination of enantiomeric purity and chiral recognition mechanism of new xanthone derivatives on (S,S)-whelk-O1 stationary phase [J].
Carraro, Maria L. ;
Palmeira, Andreia ;
Tiritan, Maria E. ;
Fernandes, Carla ;
Pinto, Madalena M. M. .
CHIRALITY, 2017, 29 (06) :247-256
[42]   Atropisomerism in bi-1,2,3-triazoles: Detection by 1H NMR using chiral shift reagents and torsional barriers calculations [J].
Santana-Martinez, Ivette ;
Bautista-Renedo, Joanatan M. ;
Ayala-Bueno, Sabrina V. ;
Zavala-Segovia, Nieves ;
Gonzalez-Rivas, Nelly ;
Corona-Becerril, David ;
Cuevas-Yanez, Erick .
JOURNAL OF MOLECULAR STRUCTURE, 2022, 1270
[43]   Determination of Enantiomeric Purity of GSK962040 Based on Liquid Chromatography Using Chiral Stationary Phase Combined with a Pre-column Derivatization Procedure [J].
Ye, Tinghong ;
Liao, Mengya ;
Hu, Mingxing ;
Xie, Yongmei ;
Zhang, Yiwen .
CHROMATOGRAPHIA, 2017, 80 (08) :1257-1262
[44]   Determination of Enantiomeric Purity of GSK962040 Based on Liquid Chromatography Using Chiral Stationary Phase Combined with a Pre-column Derivatization Procedure [J].
Tinghong Ye ;
Mengya Liao ;
Mingxing Hu ;
Yongmei Xie ;
Yiwen Zhang .
Chromatographia, 2017, 80 :1257-1262
[45]   Chiral capillary electrophoretic determination of the enantiomeric purity of homocamptothecin derivatives, promising antitumor topoisomerase I inhibitors, using highly sulfated CDs and fluorescence detection [J].
Goossens, Jean-Francois ;
Mahieu, Christine ;
Dias, Nathalie ;
Bailly, Christian ;
Principe, Paola ;
Bonte, Jean-Paul ;
Lansiaux, Amelie ;
Vaccher, Claude ;
Foulon, Catherine .
ELECTROPHORESIS, 2006, 27 (23) :4717-4729
[46]   LC determination of the enantiomeric purity of levamisole using stationary phase with bonded naphthylethylcarbamoylated-β-cyclodextrin [J].
Dolezalová, M ;
Tkaczyková, M .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2001, 25 (3-4) :407-415
[47]   Preparative HPLC separation of methoxytetralins, ligands for melatonin receptors, containing two chiral centers with polysaccharide chiral stationary phases. Determination of enantiomeric purity [J].
Lipka, E ;
Guelzim, A ;
Yous, S ;
Bonte, JP ;
Vaccher, C .
JOURNAL OF BIOCHEMICAL AND BIOPHYSICAL METHODS, 2005, 64 (01) :46-58
[48]   Efficient 1H NMR chiral discrimination of sulfoxides caused by the dynamic nature of (R,R)-3′,3"-biBINOL [J].
Kawanami, Toshio ;
Ishizuka, Kentaro ;
Furuno, Hiroshi ;
Shiota, Yoshihito ;
Yoshizawa, Kazunari ;
Inanaga, Junji .
TETRAHEDRON-ASYMMETRY, 2017, 28 (11) :1587-1590
[49]   A validated chiral HPLC method for the determination of enantiomeric purity of R-β-amino-β-(4-methoxyphenyl) propionic acid [J].
Madhavan, P. ;
Rao, B. M. ;
Pravin ;
Abhishek ;
Kumar, P. R. ;
Sreenivasulu, M. ;
Chandrasekhar, K. B. .
CHROMATOGRAPHIA, 2007, 65 (1-2) :81-84
[50]   A Validated Chiral HPLC Method for the Determination of Enantiomeric Purity of R-β-amino-β-(4-methoxyphenyl) Propionic Acid [J].
P. Madhavan ;
B. M. Rao ;
P. R. Pravin ;
M. Abhishek ;
K. B. Kumar .
Chromatographia, 2007, 65 :81-84
12345