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Fragmentation study of simvastatin and lovastatin using electrospray ionization tandem mass spectrometry

✍ Scribed by Hong Wang; Yunhui Wu; Zhongxi Zhao

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
302 KB
Volume
36
Category
Article
ISSN
1076-5174

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✦ Synopsis

The fragmentation mechanism of simvastatin and lovastatin was investigated using both triple quadrupole and ion trap mass spectrometers. The elimination of the ester side-chain followed by dehydration and dissociation of the lactone moiety were observed as the main fragmentation pathways for both compounds. Another major fragmentation process was a C==C double-bond facilitated rearrangement. Our tandem mass spectrometric (MS/MS) data suggested that the beta-hydroxy group was involved in the fragmentation by interacting with the carboxyl group generated from the ring opening of the lactone. As a result, a facile neutral loss of 60 Da (CH(3)COOH or a combination of CH(2)==C==O and H(2)O) was detected. MS/MS studies of the structural analogs also provided evidence that the dehydration of the beta-hydroxy lactone generated preferentially the beta,gamma-unsaturated lactones.

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