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Utilisation of electrospray time-of-flight mass spectrometry for solving complex fragmentation patterns: application to benzoxazinone derivatives

AutorBonnington, Lea; Barceló, Damià; Knepper, Thomas P.
Palabras claveElectrospray time-of-flight-mass spectrometry (ESI-TOFMS)
Structural elucidation
fragmentation patterns
Fecha de publicación16-oct-2003
CitaciónJournal of Mass Spectrometry 38(10): 1054-1066 (2003)
ResumenIn this paper we describe the application of electrospray time-of-flight mass spectrometry (ESI-TOFMS) to structural elucidation of the fragment ions formed from a range of natural and synthetic allelochemical derivatives. The extensive mass spectrometric characterisation of ten non-glucosylated benzoxazinone derivatives using this method is described here for the first time. The analytes include six naturally occurring 1,4-benzoxazin-3(4H)-one derivatives, including the hydroxamic acids DIMBOA [2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one] and DIBOA [2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one], lactams HBOA [2-hydroxy-2H-1,4-benzoxazin-3(4H)-one] and HMBOA [2-hydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one], benzoxazolinones BOA [benzoxazolin-2(3H)-one] and MBOA [6-methoxy-benzoxazolin-2(3H)-one] and four synthetic variations, 2H-DIBOA [4-hydroxy-2H-1,4-benzoxazin-3(4H)-one], 2OMe-DIBOA [2-methoxy-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one], 2H-HBOA [2H-1,4-benzoxazin-3(4H)-one] and 2OMe-HBOA [2-methoxy-2H-1,4-benzoxazin-3(4H)-one]. Assignments of the mass spectral fragments were aided by elemental composition calculation results, comparison of structural analogues and background literature, and acquired knowledge regarding feasible structures for the compounds. The influence of substituents on the chemical reactivity of the compounds with respect to the observed MS behaviour over varying nozzle potentials is addressed and, through comparison of the structural analogues, generic fragmentation patterns have also been identified.
Descripción13 pages, 5 figures, 2 tables.-- PMID: 14595855 [PubMed].
Versión del editorhttp://dx.doi.org/10.1002/jms.519
ISSN1076-5174 (Print)
1096-9888 (Online)
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