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Reactions of dinitrogen pentoxide and nitrogen dioxide with 1‐palmitoyl‐2‐oleoyl‐ sn ‐glycero‐3‐phosphocholine
Author(s) -
Lai C. C.,
FinlaysonPitts B. J.
Publication year - 1991
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/bf02537142
Subject(s) - phosphocholine , lipidology , nitrogen , chemistry , nitrogen dioxide , clinical chemistry , niobium pentoxide , inorganic chemistry , organic chemistry , phospholipid , biochemistry , membrane , niobium , phosphatidylcholine
The reactions of gaseous dinitrogen pentoxide (N 2 O 5 ) and nitrogen dioxide (NO 2 ) with 1‐palmitoyl‐2‐oleoyl‐ sn ‐glycero‐3‐phosphocholine (POPC) coated on the inside surface of a glass reaction cell were studied at 298 K. Unsaturated phosphatidylcholines are significant components of pulmonary surfactant in the alveolar region of the lung and hence serve as a simple model to examine reactions of pulmonary surfactant with these oxidant air pollutants. Using high‐performance liquid chromatography (HPLC), Fourier transform infrared and fast atom bombardment mass spectroscopy, the major products of reactions of POPC with N 2 O 5 and NO 2 were separated and identified. In the POPC‐N 2 O 5 reaction using either air or helium as a buffer gas, the nitronitrate, vinyl nitro and allylic nitro derivatives, as well as a small amount of the trans ‐isomer of the starting material, were obtained. The nature of the products obtained from the POPC‐NO 2 reaction depends on the concentration of NO 2 as well as whether air is present. At low NO 2 concentrations (P NO 2 / N 2 O 4 ≤3.8 Torr) in air or in helium, the trans ‐isomer of POPC was formed almost exclusively. At higher NO 2 concentrations (P NO 2 /N 2 O 4 ≥20 Torr) in helium, the dinitro, vinyl nitro and nitro alcohol derivatives were formed. In the presence of air (or 24% 18 O 2 in helium), a nitronitrate and a dinitronitrate were additional products. Mechanisms for the formation of the observed products and implications for the inhalation of oxides of nitrogen are discussed.