Document Detail


Stereochemical differentiation of C-7 hydroxyltaxane isomers by electrospray ionization mass spectrometry.
MedLine Citation:
PMID:  19125430     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
In this study, different electrospray ionization mass spectrometric (ESI-MS) methods were utilized to analyze several pairs of taxane stereoisomers including paclitaxel and 7-epi-paclitaxel. Both ESI-MS and tandem mass spectrometry (MS/MS) techniques provided stereochemically dependent mass spectra in negative-ion mode, and all studied stereoisomers could be easily distinguished based on their characteristic ions or distinct fragmentation patterns. MS/MS experiments for several taxane analogues at various collision energies were performed to elucidate potential dissociation pathways. The gas-phase deprotonation potentials were also calculated to estimate the most thermodynamically favorable deprotonation site using DFT B3LYP/6-31G(d). The results of the theoretical studies agreed well with the fragmentation patterns of paclitaxel and 7-epi-paclitaxel observed from MS/MS experiments. In addition, it was found that liquid chromatography (LC)/ESI-MS was a useful and sensitive technique for assignment of C-7 taxane stereoisomers from realistic samples.
Authors:
Guang-Bo Ge; Rong Zhang; Chun-Zhi Ai; Yu-Qi He; Yan-Yan Zhang; Xing-Bao Liu; Li Yang; Zheng-Tao Wang; Ling Yang
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Rapid communications in mass spectrometry : RCM     Volume:  23     ISSN:  0951-4198     ISO Abbreviation:  Rapid Commun. Mass Spectrom.     Publication Date:  2009 Feb 
Date Detail:
Created Date:  2009-01-13     Completed Date:  2009-03-06     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8802365     Medline TA:  Rapid Commun Mass Spectrom     Country:  England    
Other Details:
Languages:  eng     Pagination:  425-32     Citation Subset:  IM    
Copyright Information:
Copyright 2009 John Wiley & Sons, Ltd.
Affiliation:
Laboratory of Pharmaceutical Resource Discovery, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, China.
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MeSH Terms
Descriptor/Qualifier:
Chromatography, Liquid / methods
Models, Molecular
Molecular Structure
Paclitaxel / chemistry
Sensitivity and Specificity
Spectrometry, Mass, Electrospray Ionization / methods*
Stereoisomerism
Taxoids / chemistry*
Chemical
Reg. No./Substance:
0/7-epipaclitaxel; 0/Taxoids; 33069-62-4/Paclitaxel

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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