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Characterization of pyoverdins and their hydrolytic degradation products by fast atom bombardment and tandem mass spectrometry
Author(s) -
Michels J.,
Taraz K.
Publication year - 1991
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.1210261017
Subject(s) - chemistry , fast atom bombardment , moiety , quinoline , tandem mass spectrometry , chromophore , hydrolysis , mass spectrometry , benzothiazole , stereochemistry , fragmentation (computing) , siderophore , organic chemistry , chromatography , biochemistry , computer science , gene , operating system
All types of pyoverdins (siderophores produced by Pseudomonas strains) have the following ‘chromophore’ substructure in common: (1S)‐5‐amino‐2,3‐dihydro‐8,9‐dihydroxy‐lH‐pyrimido[l,2‐α]quinoline‐1‐carboxyhic acid. Its hydrolysis product, (1S)‐2,3‐dihydro‐5,8,9‐trihydroxy‐lH‐pyrimido[l,2‐α]quinoline‐1‐carboxylic acid, has been isolated and analysed for the first time by means of fast atom bombardment (FAB) and tandem mass spectrometry. This allows the pyoverdin chromophore to be identified. It was established that the fragmentation of pyoverdin [M + H] + ions under FAB conditions is initiated by a retro‐Diels‐Alder decomposition of the tetrahydropyrimidine ring of the chromophore moiety, contributing to the structure elucidation of pyoverdins.