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Gas-phase fragmentation study of a novel series of synthetic 2-oxo-2H-benzopyrano[2,3-d]pyrimidine derivatives using electrospray ionization tandem mass spectroscopy measured with a quadrupole orthogonal time-of-flight hybrid instrument.
Rapid Commun Mass Spectrom. 2009 Jan; 23(2):267-81.RC

Abstract

The fragmentation patterns of a series of six novel synthesized benzopyranopyrimidine derivatives 1-6, possessing the same 2-oxo-2H-benzopyrano[2,3-d]pyrimidine backbone structure, were investigated by electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS) techniques using a quadrupole orthogonal time-of-flight (QqToF)-hybrid instrument. The series of six pure benzopyranopyrimidine compounds contained three constitutional isobaric isomers (compounds 4-6). A simple methodology, based on the use of ESI (positive ion mode) and increasing the declustering potential in the atmospheric pressure/vacuum interface resulting in collision-induced dissociation (CID), was used to enhance the formation of the product ions. In general, the novel synthetic benzopyranopyrimidine derivatives 1-6 afforded exact accurate masses for the protonated molecules. This led to the confirmation of both molecular masses and chemical structures of the studied compounds. The breakdown routes of the protonated molecules were rationalized by conducting low-energy CID-MS/MS analyses. It was shown that the MS/MS fragmentation routes for the protonated molecules 1 and 2 were similar, and that the MS/MS fragmentations of the constitutional isobaric protonated molecules 5 and 6 were identical. It was also shown that the gas-phase CID fragmentations of 5 and 6 were different from that of their constitutional isomer 4. Finally, the ESI-MS and CID-MS/MS analyses of the protonated molecules that were obtained from the monodeuterated benzopyranopyrimidine derivatives 1-6 confirmed the values obtained for the exact masses, the precise structural assignments of all product ions and all the pathways described in the proposed CID fragmentations.

Authors+Show Affiliations

Chimie Appliquée: Héterocycles, Corps Gras et Polymères, Faculté des Sciences, 3038 Sfax, Tunisia.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Evaluation Study
Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19089859

Citation

Turki, Hamida, et al. "Gas-phase Fragmentation Study of a Novel Series of Synthetic 2-oxo-2H-benzopyrano[2,3-d]pyrimidine Derivatives Using Electrospray Ionization Tandem Mass Spectroscopy Measured With a Quadrupole Orthogonal Time-of-flight Hybrid Instrument." Rapid Communications in Mass Spectrometry : RCM, vol. 23, no. 2, 2009, pp. 267-81.
Turki H, Genestie B, Gharbi RE, et al. Gas-phase fragmentation study of a novel series of synthetic 2-oxo-2H-benzopyrano[2,3-d]pyrimidine derivatives using electrospray ionization tandem mass spectroscopy measured with a quadrupole orthogonal time-of-flight hybrid instrument. Rapid Commun Mass Spectrom. 2009;23(2):267-81.
Turki, H., Genestie, B., Gharbi, R. E., Boussiry, S. E., & Banoub, J. (2009). Gas-phase fragmentation study of a novel series of synthetic 2-oxo-2H-benzopyrano[2,3-d]pyrimidine derivatives using electrospray ionization tandem mass spectroscopy measured with a quadrupole orthogonal time-of-flight hybrid instrument. Rapid Communications in Mass Spectrometry : RCM, 23(2), 267-81. https://doi.org/10.1002/rcm.3876
Turki H, et al. Gas-phase Fragmentation Study of a Novel Series of Synthetic 2-oxo-2H-benzopyrano[2,3-d]pyrimidine Derivatives Using Electrospray Ionization Tandem Mass Spectroscopy Measured With a Quadrupole Orthogonal Time-of-flight Hybrid Instrument. Rapid Commun Mass Spectrom. 2009;23(2):267-81. PubMed PMID: 19089859.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Gas-phase fragmentation study of a novel series of synthetic 2-oxo-2H-benzopyrano[2,3-d]pyrimidine derivatives using electrospray ionization tandem mass spectroscopy measured with a quadrupole orthogonal time-of-flight hybrid instrument. AU - Turki,Hamida, AU - Genestie,Benoit, AU - Gharbi,Rachid El, AU - Boussiry,Sameh El, AU - Banoub,Joseph, PY - 2008/12/18/entrez PY - 2008/12/18/pubmed PY - 2009/3/18/medline SP - 267 EP - 81 JF - Rapid communications in mass spectrometry : RCM JO - Rapid Commun Mass Spectrom VL - 23 IS - 2 N2 - The fragmentation patterns of a series of six novel synthesized benzopyranopyrimidine derivatives 1-6, possessing the same 2-oxo-2H-benzopyrano[2,3-d]pyrimidine backbone structure, were investigated by electrospray ionization mass spectrometry (ESI-MS) and tandem mass spectrometry (MS/MS) techniques using a quadrupole orthogonal time-of-flight (QqToF)-hybrid instrument. The series of six pure benzopyranopyrimidine compounds contained three constitutional isobaric isomers (compounds 4-6). A simple methodology, based on the use of ESI (positive ion mode) and increasing the declustering potential in the atmospheric pressure/vacuum interface resulting in collision-induced dissociation (CID), was used to enhance the formation of the product ions. In general, the novel synthetic benzopyranopyrimidine derivatives 1-6 afforded exact accurate masses for the protonated molecules. This led to the confirmation of both molecular masses and chemical structures of the studied compounds. The breakdown routes of the protonated molecules were rationalized by conducting low-energy CID-MS/MS analyses. It was shown that the MS/MS fragmentation routes for the protonated molecules 1 and 2 were similar, and that the MS/MS fragmentations of the constitutional isobaric protonated molecules 5 and 6 were identical. It was also shown that the gas-phase CID fragmentations of 5 and 6 were different from that of their constitutional isomer 4. Finally, the ESI-MS and CID-MS/MS analyses of the protonated molecules that were obtained from the monodeuterated benzopyranopyrimidine derivatives 1-6 confirmed the values obtained for the exact masses, the precise structural assignments of all product ions and all the pathways described in the proposed CID fragmentations. SN - 0951-4198 UR - https://www.unboundmedicine.com/medline/citation/19089859/Gas_phase_fragmentation_study_of_a_novel_series_of_synthetic_2_oxo_2H_benzopyrano[23_d]pyrimidine_derivatives_using_electrospray_ionization_tandem_mass_spectroscopy_measured_with_a_quadrupole_orthogonal_time_of_flight_hybrid_instrument_ L2 - https://doi.org/10.1002/rcm.3876 DB - PRIME DP - Unbound Medicine ER -