Abstract
Myeloperoxidase released from stimulated neutrophils is able to produce hypochlorous and hypobromous acids. The composition of the reaction products of the interaction of hypohalous acid with double bonds of phosphatidylcholines was analysed by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry using reagents enriched in 16 O , 18 O , 35 Cl , 37 Cl , 79 Br , or 81 Br . Two different types of products were assigned according to the mass spectra. First, chlorohydrins as well as bromohydrins were formed whereby the oxygen introduced was derived from water as shown by using H 2 16 O or H 2 18 O . In the second product a hydrogen atom was replaced by a halogen. This was clearly evidenced by different mass shifts using chlorine or bromine isotopes and the lack of any effects by oxygen isotopes. These results are consistent with the view that two principal possibilities of stabilisation of π-complexes formed after binding of Cl + or Br + to the π-system of the double bond exist.
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