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

Р. Т. ТлегеновKarakalpak State University, Universitetskaya 1, 742012 Nukus City, Republic of KarakalpakstanJaana M. H. PakarinenUniversity of Joensuu, Department of Chemistry, P. O. Box 111, FI-80101 Joensuu, FinlandL. OresmaaUniversity of Joensuu, Department of Chemistry, P. O. Box 111, FI-80101 Joensuu, FinlandMarkku AhlgrénUniversity of Joensuu, Department of Chemistry, P. O. Box 111, FI-80101 Joensuu, FinlandPirjo VainiotaloUniversity of Joensuu, Department of Chemistry, P. O. Box 111, FI-80101 Joensuu, Finland
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Abstract magnified image 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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