Abstract

European Journal of Mass Spectrometry
Volume 16 Issue 4, Pages 489–501 (2010)
doi: 10.1255/ejms.1071

Rearrangement and fragmentation of estrogen ether ions: new aspects found with a Fourier transform ion cyclotron resonance mass spectrometry

Christoph Freudenhammer and Jürgen Grotemeyer
Institute of Physical Chemistry, Christian-Albrechts University at Kiel, Ludewig-Meyn-Straße 8, 24098 Kiel, Germany. E-mail: grote@phc.uni- kiel.de

Electrospray ionization (ESI) mass spectra of several di- and tri-hydroxy-estratriene-ethers as well as estradiol and estriol have been investigated by high resolution mass spectrometry. The fragmentation mechanisms leading to the loss of water molecules from the protonated molecular ion have been rationalized by using protecting groups as well as mass spectrometric means like collision induced dissociation (CID) and infra-red multi photon dissociation (IRMPD). The unexpected observation of a simultaneous loss of two water molecules from the protonated estradiol ethers and of three water molecules from the protonated Estriol ethers has been discussed with respect to varying reaction mechanisms and rearrangements. Results and conclusions derived from them were obtained by adequate deuterated ethers.

Keywords: fragmentation mechanism, mass spectrometry, ion cyclotron resonance, electrospray ionization, internal energy, structure determination

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