Red cell membrane and plasma linoleic acid nitration products: Synthesis, clinical identification, and quantitation

Baker et al. 10.1073/pnas.0402587101.

Supporting Information

Files in this Data Supplement:

Supporting Figure 4
Supporting Figure 5

Supporting Figure 4

Fig. 4. Synthesis and purification of nitrated linoleic acid (LNO₂). (A) Linoleic acid is nitrated by reaction with phenylselenium bromide in tetrahydrofuran/acetonitrile (50:50, vol/vol) in the presence of HgCl₂ and NaNO₂ (I–III). The phenylselenium adduct is oxidized by H₂O₂ to generate linoleic acid that is nitrated predominantly at the 10-carbon and 12-carbon. (B) Nitrated linoleic acid positional isomers are purified from the crude reaction mixture by thin-layer chromatography. The major positional isomers have R_f values of 0.45 and 0.50 for the C10 and C12 positional isomers, respectively.

Supporting Figure 5

Fig. 5. Spectral analysis of LNO₂. (A) Nitrated linoleic acid has a unique absorbance maximum at 329 nm in basic methanol (2% 1M NaOH). (B) By measuring the absorbance of increasing concentrations of LNO₂ at 329 nm, the extinction coefficient was determined to be e = 10.1 cm^–1•M^–1.