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Evaluation of fast atom bombardment mass spectrometric and low‐energy collisional activation tandem mass spectrometric data for the structural elucidation of bisbenzylisoquinoline alkaloids
Author(s) -
Caldwell Gary W.,
Masucci John A.,
Wu WuNan
Publication year - 1994
Publication title -
organic mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0030-493X
DOI - 10.1002/oms.1210290503
Subject(s) - chemistry , fragmentation (computing) , fast atom bombardment , tandem , ether , mass spectrum , ion , tandem mass spectrometry , polyatomic ion , mass spectrometry , stereochemistry , medicinal chemistry , computational chemistry , analytical chemistry (journal) , organic chemistry , chromatography , materials science , computer science , composite material , operating system
The fast atom bombardment (FAB) mass spectra and low‐energy collisional activation mass spectra of ions generated under FAB were investigated for twelve bisbenzylisoquinoline (BBI) alkaloids. The relative molecular mass of the free base and diquaternary BBI alkaloids can be obtained from FAB data. However, monoquaternary ammonium salts produce only an [M — X] + ion and the relative molecular mass cannot be determined. For Type A (single ether linkage) BBI alkaloids, fragmentation occurs primarily from benzylic and ether cleavages. Thus, the total number of aromatic substituents (OH, OCH 3 or OCH 2 O) can be determined for rings A‐B, C‐D, E and F. For Type B (two either linkages) BBI alkaloids, fragmentation occurs primarily from double benzylic cleavages. Hence only the total number of aromatic substituents can be determined for the upper half of the Type B BBI alkaloids, i.e. rings A‐B and C‐D. An unknown alkaloid was examined to illustrate the utility of the fragmentation schemes.