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Gas‐phase fragmentation of γ‐lactone derivatives by electrospray ionization tandem mass spectrometry

2009; Wiley; Volume: 44; Issue: 12 Linguagem: Inglês

10.1002/jms.1682

1096-9888

Antônio Eduardo Miller Crotti, Érika Soares Bronze‐Uhle, Paulo Gustavo Barboni Dantas Nascimento, Paulo Marcos Donate, Sérgio E. Galembeck, Ricardo Vessecchi, Norberto Peporine Lopes,

Metabolomics and Mass Spectrometry Studies

Abstract Fragmentation reactions of β‐hydroxymethyl‐, β‐acetoxymethyl‐ and β‐benzyloxymethyl‐butenolides and the corresponding γ‐butyrolactones were investigated by electrospray ionization tandem mass spectrometry (ESI‐MS/MS) using collision‐induced dissociation (CID). This study revealed that loss of H 2 O [M + H −18] + is the main fragmentation process for β‐hydroxymethylbutenolide (1) and β‐hydroxymethyl‐γ‐butyrolactone (2). Loss of ketene ([M + H −42] + ) is the major fragmentation process for protonated β‐acetoxymethyl‐γ‐butyrolactone (4), but not for β‐acetoxymethylbutenolide (3). The benzyl cation ( m / z 91) is the major ion in the ESI‐MS/MS spectra of β‐benzyloxymethylbutenolide (5) and β‐benzyloxymethyl‐γ‐butyrolactone (6). The different side chain at the β‐position and the double bond presence afforded some product ions that can be important for the structural identification of each compound. The energetic aspects involved in the protonation and gas‐phase fragmentation processes were interpreted on the basis of thermochemical data obtained by computational quantum chemistry. Copyright © 2009 John Wiley & Sons, Ltd.