The hydrogenation of phospholipid-bound unsaturated fatty acids by a homogeneous, water-soluble, palladium catalyst.
The hydrogenation of unsaturated phospholipids by palladium di(sodium alizarine monosulphonate) activated for 5 min under H2 proceeded rapidly at 20 degrees C and 1 atm. H2. Multibilayer liposomes of dioleoyl- and dilinolenoylphosphatidylcholine were hydrogenated at similar rates while dilinoleoyl- and 1-palmitoyl-2-oleoylphosphatidylcholine were hydrogenated at slightly slower rates. The reduction of polyunsaturated fatty acids gave rise to a variety of natural and unnatural positional cis and trans isomers which were largely reduced further to saturated fatty acids as the hydrogenation continued. Dioleoylphosphatidylethanolamine was attacked by the catalyst more slowly at 20 degrees C than was the equivalent phosphatidylcholine molecular species. Experiments conducted using mixtures of phosphatidylethanolamine and phosphatidylcholine in varying proportions also suggested that phospholipids are slightly more susceptible to catalytic hydrogenation in the bilayer phase than in the hexagonalII phase. Understanding the sequence of hydrogenation reactions involving these one and two component lipid preparations is useful in interpreting the action of the palladium catalyst on living cells under the same mild conditions.
D002384:Catalysis; D005231:Fatty Acids, Unsaturated / Q000378:metabolism*; D006865:Hydrogenation; D007700:Kinetics; D008051:Lipid Bilayers / Q000378:metabolism; D008081:Liposomes / Q000378:metabolism*; D009942:Organometallic Compounds / Q000378:metabolism*; D010713:Phosphatidylcholines / Q000378:metabolism; D010714:Phosphatidylethanolamines / Q000378:metabolism; D010743:Phospholipids / Q000378:metabolism*; D013329:Structure-Activity Relationship
D005231:Fatty Acids, Unsaturated; D008051:Lipid Bilayers; D008081:Liposomes; D009942:Organometallic Compounds; D010713:Phosphatidylcholines; D010714:Phosphatidylethanolamines; D010743:Phospholipids; C044770:palladium sulfonated alizarine