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Mass spectral study of derivatives of the four bilirubin‐IX isomers
Author(s) -
Compernolle F.,
Blanckaert N.,
Heirwegh K. P. M.
Publication year - 1976
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200030403
Subject(s) - chemistry , fragmentation (computing) , trimethylsilyl , deuterium , mass spectrum , medicinal chemistry , yield (engineering) , mass spectrometry , chromatography , materials science , physics , quantum mechanics , computer science , metallurgy , operating system
The β, γ and δ isomers of bilirubin‐IX show a decreased stability as compared with the IXα isomer; characteristic mass spectra are obtained only for the tetrakis‐(trimethylsilyl) derivatives of the IXα and IXγ isomers. Hydrogenation of the vinyl substituents increases the thermal stability of the bilirubins and gives rise to a characteristic mass spectrum for the tetrakis‐(trimethylsilyl) derivative of meso ‐bilirubin‐IXδ. The ethyl anthranilate azopigments derived from the four bilirubins yield characteristic mass spectra, except for the two unstable divinyl substituted azodipyrroles (mol.wt. 416), derived from bilirubin‐IXβ and IXδ. The corresponding mol.wt. 420 azopigments derived from the hydrogenated bilirubins are thermally stable. Elucidation of mass spectral fragmentation pathways is facilitated by the varying positions of the substituents and by deuterium labelling, and permits the assignment of structures to the various isomeric azodipyrroles.