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Application of site‐selective ion–molecule reactions to the analysis of the cinchona alkaloids
Author(s) -
Eichmann Erika S.,
Brodbelt Jennifer S.
Publication year - 1993
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.1210281237
Subject(s) - cinchonidine , cinchonine , quinidine , chemistry , cinchona alkaloids , quinine , cinchona , molecule , selectivity , stereoselectivity , reagent , organic chemistry , stereochemistry , enantioselective synthesis , catalysis , medicine , malaria , immunology , pharmacology , biology
Functional group interactions within biologically relevant molecules are among the most influential yet least understood factors in determining their reactive behaviors. Reactions of dimethyl ether ions, which have previously been shown to be site‐selective, with four cinchona alkaloids, cinchonine, cinchonidine, quinine and quinidine, have been examined. These reactions are each shown to produce qualitatively similar spectra for the stereoisomeric pairs cinchonidine–cinchonine and quinidine–quinine, but small variations in the relative abundances of the products indicate that some stereoselectivity can be observed. The site selectivity of each of the reagents was investigated by observing the reactions occurring with model subunits of the alkaloids.