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Updated: Nov 22, 2025

Free Radicals in Chemical Biology: from Chemical Behavior to Biomarker Development
Published on: April 15, 2013
OH radical reactions with the hydrophilic component of sphingolipids
Alexandra Lisovskaya1, Oleg Shadyro2, Olav Schiemann3
1Notre Dame Radiation Laboratory, University of Notre Dame, Notre Dame, 46556 Indiana, USA. alisousk@nd.edu and Institute of Physical and Theoretical Chemistry, University of Bonn, Wegelerstr. 12, 53115, Bonn, Germany.
Abstract:
In this work, using the example of model compounds, we studied the reactions resulting from the interaction of OH radicals with the hydrophilic part of sphingolipids. We compared the stopped-flow EPR spectroscopy and pulse radiolysis with optical detection methods to characterize radical intermediates formed in the reaction of OH radicals with glycerol, serinol and N-boc-serinol. Quantum chemical calculations were also performed to help interpret the observed experimental data. It was shown that H-abstraction from the terminal carbon atom is the main process that is realized for all the studied compounds. The presence of the unsubstituted amino group (-NH2) is seen to completely change the reaction properties of serinol in comparison with those observed in glycerol and N-boc serinol.
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