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Analysis of folacin by GC/MS: Structures and mass spectra of fluorinated derivatives of para ‐aminobenzoyl glutamic acid
Author(s) -
Toth John P.,
Gregory Jesse F.
Publication year - 1988
Publication title -
biomedical and environmental mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0887-6134
DOI - 10.1002/bms.1200170203
Subject(s) - trifluoroacetic anhydride , chemistry , trifluoroacetic acid , mass spectrum , acylation , yield (engineering) , ion , mass spectrometry , deuterium , glutamic acid , ring (chemistry) , medicinal chemistry , amino acid , organic chemistry , chromatography , catalysis , biochemistry , physics , materials science , quantum mechanics , metallurgy
Simultaneous acylation/esterification of para ‐aminobenzoyl glutamic acid with trifluoroacetic anhydride and trifluoroethanol was attempted as part of a scheme to monitor deuterium‐labeled dietary folates at nanogram levels in human subjects by GCMS. The anticipated fully‐derivatized product comprised only about 10% of the reaction mixture; EI, positive ion CI and electron capture negative ion mass spectra of the major product (ca 80% yield) are consistent with a cyclic compound, most likely a lactam with a 5‐membered ring. The stability and mass spectral characteristics of the cyclic compound permit differentiation of isotopically labeled species at subnanogram levels by selected ion monitoring in the electron capture negative ion mode.