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Synthesis and characterization of some derivatives of lupinine and aminolupinine. Collision induced dissociation mass spectrometry studies of protonated molecules

✍ Scribed by Rust T. Tlegenov; Jaana M. H. Pakarinen; Larisa Oresmaa; Markku Ahlgrén; Pirjo Vainiotalo

Publisher
Journal of Heterocyclic Chemistry
Year
2007
Tongue
English
Weight
498 KB
Volume
44
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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Some ester, amide and thioether derivatives of lupinine, aminolupinine and bromolupinine were synthesized and characterized in order to search biologically active compounds. The protonated molecules were studied by tandem mass spectrometry using collision induced dissociation (CID) technique in order to find out how different structural features and functional groups in different quinolizidine derivatives influence fragmentation behavior. Some theoretical calculations were also made to clarify the conformations of neutral and protonated molecules, to reveal the fragmentation routes and the product ions obtained. The functional groups clearly directed the fragmentations although the typical fragments for lupinine were still observed in all the cases. Theoretical calculations were in agreement with observed fragmentations and greatly helped interpretation of the CID spectra.

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