Phospholipids containing photoactivable groups in studies of biological membranes.
Photoactivable carbene precursors, aryl diazirines and trifluorodiazopropionates, were incorporated synthetically into the omega-positions of fatty acids, which were used to synthesize phospholipids. Extensive intermolecular C--H insertion reactions were demonstrated by photolysis of liposomes prepared from the above phospholipids. Structural analysis of the cross-linked products showed that the predominant sites of cross-linking were in the expected positions within the bilayer. Studies on the topography of a number of membrane proteins using the above phospholipids were initiated. Cross-linking of the photoactivable phospholipids to membrane-embedded proteins, glycophorin A, cytochrome b5, and gramicidin A, was demonstrated.
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D003432:Cross-Linking Reagents; D003580:Cytochromes / Q000032:analysis; D005227:Fatty Acids / Q000138:chemical synthesis; D006021:Glycophorins / Q000032:analysis; D006096:Gramicidin / Q000032:analysis; D006801:Humans; D007202:Indicators and Reagents; D008565:Membrane Proteins / Q000032:analysis; D008566:Membranes / Q000032:analysis*; D010743:Phospholipids / Q000138:chemical synthesis / Q000528:radiation effects; D010777:Photochemistry; D011817:Rabbits
D003432:Cross-Linking Reagents; D003580:Cytochromes; D005227:Fatty Acids; D006021:Glycophorins; D007202:Indicators and Reagents; D008565:Membrane Proteins; D010743:Phospholipids; D006096:Gramicidin