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Alloxazines and iso alloxazines. Mass spectrometric analysis of riboflavin and related compounds
Author(s) -
Brown Peter,
Hornbeck Cecil L.,
Cronin John R.
Publication year - 1972
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.1210061215
Subject(s) - riboflavin , chemistry , mass spectrum , pyrimidine , fragmentation (computing) , flavin group , decomposition , metastability , mass spectrometry , ion , ring (chemistry) , computational chemistry , medicinal chemistry , stereochemistry , chromatography , organic chemistry , biochemistry , computer science , enzyme , operating system
The positive ion electron‐impact mass spectra of a series of alloxazines, iso ‐alloxazines and some derivatives have been examined. The compounds employed were lumichrome (7,8‐dimethylalloxazine), 1,3‐dimethyllumichrome, lumiflavin (7,8,10‐trimethyl‐ iso ‐alloxazine), 3‐methyllumiflavin, riboflavin [7,8‐dimethyl‐10‐(D‐1′‐ribityl)‐ iso ‐alloxazine], riboflavin tetraacetate, 3‐methylriboflavin tetraacetate and riboflavin tetrapropionate. By using exact mass measurements, metastable ion defocusing and the mass/composition shifts occurring with derivatives, it has been possible to arrive at detailed interpretations of the mass spectra of all compounds. With lumichrome and lumiflavin, fragmentation commences by elimination of HNCO from the pyrimidine ring. With riboflavin and its derivatives the ribityl chain cleaves off first, followed by decomposition of the iso ‐alloxazine ring. Application of these methods and findings to the structural analysis of chemically interesting modified flavins is predicted to be rewarding.