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Atmospheric pressure chemical ionization multi‐stage mass spectrometry in the characterization of stereoisomeric synthons of cyclopropane amino acids
Author(s) -
Cristoni Simone,
Cativiela Carlos,
Jiménez Ana I.,
Traldi Pietro
Publication year - 2000
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/(sici)1096-9888(200002)35:2<199::aid-jms930>3.0.co;2-6
Subject(s) - chemistry , cyclopropane , mass spectrometry , synthon , fragmentation (computing) , molecule , ion , ionization , methanol , chemical ionization , solvent , stereochemistry , atmospheric pressure , analytical chemistry (journal) , medicinal chemistry , organic chemistry , chromatography , ring (chemistry) , computer science , operating system , oceanography , geology
The mass spectrometric behaviour of (1 S ,2 R )‐, (1 R ,2 R )‐, (1 R ,2 S )‐ and (1 S ,2 S )‐2‐[( S )‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl]‐1‐spiro‐{4′[2′‐phenyl‐5′(4′H)‐oxazolone]} cyclopropane (2) and (1 S ,2 R )‐, (1 R ,2 R )‐, (1 R ,2 S )‐ and (1 S ,2 S )‐methyl‐1‐benzamido‐2‐[( S )‐2,2‐dimethyl‐1,3‐dioxolan‐4‐yl]cyclopropanecarboxylate (3) was studied under atmospheric pression ionization conditions and by multi‐stage mass spectrometric (MS n ) experiments performed with an ion trap. Interestingly, by using methanol as solvent, compounds 2 lead to [M + H + CH 3 OH] + ions which, as proved by collisional experiments, exhibit the same structure of the corresponding compound 3. MS/MS of [MH] + ions allows a clear characterization of the different stereoisomers, which give rise to specific fragmentation pathways, rationalized with respect to the structure of the neutral molecules. Copyright © 2000 John Wiley & Sons, Ltd.