Letter: Separation of tautomeric forms of [2-nitrophloroglucinol-H]- by an in-electrospray ionization source hydrogen/deuterium exchange approach

Yury Kostyukevich, Alexey Kononikhin, Igor Popov, Natalia Starodubtseva, Eugene Kukaev, Eugene Nikolaev

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

Here we report the observation that, depending on the solvent used for the electrospray, 2-nitrophloroglucinol undergoes a deprotonation from different sites forming two tautomeric gas phase ions. Those ions differ by the collision-induced dissociation (CID) spectra and by the gas phase hydrogen/deuterium (H/D) exchange kinetic. We performed H/D exchange in the electrospray ionization (ESI) source by saturation ESI region with vapors of deuterated solvent (D2O). It was observed that [2- nitrophloroglucinol-H]- exchanges two -OH hydrogens when MeOD is used as the spray solvent but when the spray solvent is 50:50 MeOD/D2O we observed an additional two H/D exchanges at the aromatic ring. We propose that the reaction occurs via a keto-enol tautomerization mechanism which was found to be energetically favorable.

Original languageEnglish
Pages (from-to)345-349
Number of pages5
JournalEuropean Journal of Mass Spectrometry
Volume20
Issue number4
DOIs
Publication statusPublished - 2014
Externally publishedYes

Keywords

  • ESI
  • FT ICR
  • H/D
  • Hydrogen/deuterium exchange
  • Proteomics

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